Methyl 2,3,4-Tri-O-Isobutyryl-1-O-Trichloroacetimidoyl-Alpha-D-Glucopyranuronate

Name: Methyl 2,3,4-Tri-O-Isobutyryl-1-O-Trichloroacetimidoyl-Alpha-D-Glucopyranuronate
SKU: ACM150607968
Rating: 5 (1 reviews)

CAS

150607-96-8

Catalog Number

ACM150607968

Category

Main Products

Molecular Weight

562.80

Molecular Formula

C21H30Cl3NO10

COA MSDS SDS Spec Sheet

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Specification

Synonyms

Methyl 2,3,4-Tri-O-isobutyryl-1-O-trichloroacetimidoyl-a-D-glucopyranuronate

Appearance

White Crystalline Solid

Methyl 2,3,4-Tri-O-Isobutyryl-1-O-Trichloroacetimidoyl-α-D-Glucopyranuronate Used in the Synthesis of Morphine-3,6-Di-β-D-Glucuronide

Brown, Richard T., et al. Tetrahedron, 2000, 56(38), 7591-7594.

This work produced high yielding morphine-3,6-di-β-d-glucuronide (M3,6diG) by two-step easy synthesis of morphine and methyl 2,3,4-tri-O-isobutyryl-1-O-trichloroacetimido-α-D-glucopyranosiduronate as raw material.
Synthesis procedure of M3,6diG
· Morphine-3,6-di(methyl 2,3,4-tri-O-isobutyryl-b-d-glucopyranuronate) 10:
A mixture of dried morphine (2.0 g, 7.0 mmol) and methyl 2,3,4-tri-O-isobutyryl-1-O-trichloroacetimidoyl-a-d-glucopyranuronate 5 (15.8 g, 28.1 mmol) was suspended in dry CH2Cl2 (40 mL) with 4A molecular sieves and stirred under argon at room temperature. BF3·Et2O (355 mL, 4.0 g, 28.1 mmol) was added, and after 30 minutes, nearly all starting materials had dissolved. Stirring continued for an additional 2 days. An extra 20 mL of CH2Cl2 was introduced, and the solution was washed with saturated aqueous sodium bicarbonate (50 mL), water, and brine before drying. Elution with CHCl3/MeOH (9:1) produced a crude product (8.5 g) containing approximately 80% diglucuronate and 20% excess sugar. Trituration with ethanol yielded pure morphine-3,6-diglucuronate 10 (4.6 g, 60%) in the form of colorless needles.
· Morphine-3,6-di-b-D-glucuronide 4:
The water solution of sodium hydroxide (1.5 M, 12 mL) was stirred into a suspension of the diglucuronate 10 (2.3 g, 2.1 mmol) in methanol (68 mL) and left overnight to react. Then the solution was acidified with glacial acetic acid, and the precipitate was sieved and rinsed with methanol (approximately 15 mL). Morphine-3,6-diglucuronide (1.2 g, 89%) was dried as a white solid at 60°C under high vacuum.

Methyl 2,3,4-Tri-O-Isobutyryl-1-O-Trichloroacetimidoyl-α-D-Glucopyranuronate for the Synthesis of Psilocin Glucuronide

Martin, Rafaela, et al. Forensic Science International, 2014, 237, 1-6.

There was a 2-step synthesis procedure to make psilocin glucuronic acid (PCG), the primary metabolite of psilocin, from methyl 2,3,4-tri-O-isobutyryl-1-O-trichloroacetimidoyl-α-d-glucopyranuronate.
Synthesis of psilocin glucuronide
· Methyl 1-O-[3-(2-dimethylaminoethyl)indol-4-yl]-2,3,4-O-triisobutyrylglucopyranuronate 3: Psilocin 1 (36.2 mg, 0.178 mmol) and methyl 2,3,4-tri-O-isobutyryl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate 2 (100 mg, 0.178 mmol) were mixed in 4 mL of anhydrous methylene chloride in an ice bath under a nitrogen atmosphere. BF3-Et2O (66.8 mL, 0.553 mmol) was added, and the mixture was stirred for 24 hours. Following dilution with an additional 4 mL of methylene chloride, the solution was washed with saturated aqueous sodium bicarbonate, water, and brine (8 mL each). The organic phase was dried and evaporated under reduced pressure. Flash chromatography on silica (using a methylene chloride/methanol/ammonia gradient of 90 + 10 + 2, v/v) yielded compound 3 as a brown solid (26.4 mg, 0.0436 mmol, 25%).
· Psilocin glucuronide 4: Compound 3 (26 mg, 0.0430 mmol) was stirred with methanol (5 mL) and 1.5 M sodium hydroxide (0.45 mL) at room temperature for 51 hours. Glacial acetic acid (60 mL) was then added, and the organic solvent was removed under reduced pressure. Semi-preparative HPLC on a C18 column, using a solvent mixture of methanol/water/formic acid (90 + 10 + 0.05, v/v), followed by lyophilization, produced psilocin glucuronide 4 as a white solid (12 mg, 0.0316 mmol, 74%).
Semi-preparative HPLC using methanol/water/formic acid (90 + 10 + 0.05, v/v) on a C18 column, followed by lyophilization, gave psilocin glucuronide 4 as a white solid (12 mg, 0.0316 mmol, 74%).

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