4-acetyl-5-benzyloxy-3-hydroxy-1-(tert-butyldiphenylsilyl)oxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene

Base Information

Chemical Name:4-acetyl-5-benzyloxy-3-hydroxy-1-(tert-butyldiphenylsilyl)oxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene
CAS No.:250273-72-4
Molecular Formula:C₆₅H₆₆O₉Si
Molecular Weight:1019.32
Hs Code.:

Synonyms:4-acetyl-5-benzyloxy-3-hydroxy-1-(tert-butyldiphenylsilyl)oxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene

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Chemical Property of 4-acetyl-5-benzyloxy-3-hydroxy-1-(tert-butyldiphenylsilyl)oxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene

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Technology Process of 4-acetyl-5-benzyloxy-3-hydroxy-1-(tert-butyldiphenylsilyl)oxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene

There total 1 articles about 4-acetyl-5-benzyloxy-3-hydroxy-1-(tert-butyldiphenylsilyl)oxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

: 89025-46-7
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride

: 1-[2-benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-phenyl]-ethanone

: 250273-72-4
4-acetyl-5-benzyloxy-3-hydroxy-1-(tert-butyldiphenylsilyl)oxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 1.83333h;
DOI:10.1016/S0008-6215(99)00140-8

Reference yield: 89.0%

: 250273-72-4
4-acetyl-5-benzyloxy-3-hydroxy-1-(tert-butyldiphenylsilyl)oxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene

: 250273-73-5
4-acetyl-5-benzyloxy-1,3-dihydroxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene

Guidance literature:: With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; for 0.583333h;
DOI:10.1016/S0008-6215(99)00140-8

Reference yield:

: 250273-72-4
4-acetyl-5-benzyloxy-3-hydroxy-1-(tert-butyldiphenylsilyl)oxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)benzene

: 4-acetyl-2-C-(2-O-acetyl-β-D-glucopyranosyl)-1,3,5-trihydroxybenzene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / NaOH / dioxane; H₂O / 0.58 h / 0 - 20 °C

2.1: 80 percent / pyridine / 2 h / 20 °C

3.1: H₂ / 10 percent Pd/C / ethyl acetate; ethanol / 24 h / 20 °C

3.2: 100 percent / silica gel / ethanol / 1 h / Heating

With pyridine; sodium hydroxide; hydrogen; palladium on activated charcoal; In 1,4-dioxane; ethanol; water; ethyl acetate; 1.1: Hydrolysis / 2.1: Acetylation / 3.1: Hydrogenolysis / 3.2: Rearrangement;
DOI:10.1016/S0008-6215(99)00140-8