methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside
CAS No.:382614-54-2
Molecular Formula:C₅₁H₆₁NO₁₃
Molecular Weight:896.044
Hs Code.:

Synonyms:methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside

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Chemical Property of methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside

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Technology Process of methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside

There total 5 articles about methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside 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: 62.0%

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 382614-42-8
ethyl 2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside

: 382614-72-4
methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-β-D-glucopyranosyl]-1-O-α-D-glucopyranoside

: 382614-54-2
methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside

Guidance literature:: ethyl 2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; silver trifluoromethanesulfonate; benzenesulfenyl chloride; In diethyl ether; dichloromethane; at -78 - -55 ℃; for 0.5h;

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside; In diethyl ether; dichloromethane; at -55 ℃;
DOI:10.1016/S0040-4020(01)00760-8

Reference yield:

: 3282-30-2
pivaloyl chloride

: 382614-54-2
methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 94 percent / pyridine / CH₂Cl₂

2.1: AgOTf; PhSCl; 2,6-di-tert-butyl-4-methylpyridine / diethyl ether; CH₂Cl₂ / 0.5 h / -78 - -55 °C

2.2: 62 percent / diethyl ether; CH₂Cl₂ / -55 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; silver trifluoromethanesulfonate; benzenesulfenyl chloride; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)00760-8

Reference yield:

: 201056-71-5
ethyl (5R)-4,6-O-benzylidene-1-thio-3-O-pivaloyl-β-D-glucopyranoside

: 382614-54-2
methyl 2,3,4-tri-O-benzyl-6-O-[2-deoxy-2-(O-pivaloyl)oximino-3-O-pivaloyl-4,6-O-benzylidene-1-α-D-glucopyranosyl]-1-O-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: (CF₃CO)2O; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 3.62 g / NaOAc; NH₂OH*HCl / ethanol; H₂O / 2.5 h / 52 °C

3.1: 94 percent / pyridine / CH₂Cl₂

4.1: AgOTf; PhSCl; 2,6-di-tert-butyl-4-methylpyridine / diethyl ether; CH₂Cl₂ / 0.5 h / -78 - -55 °C

4.2: 62 percent / diethyl ether; CH₂Cl₂ / -55 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; hydroxylamine hydrochloride; sodium acetate; silver trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; benzenesulfenyl chloride; In diethyl ether; ethanol; dichloromethane; water;
DOI:10.1016/S0040-4020(01)00760-8