tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(tert-butoxycarbonyl)methyl]-α-D-glucopyranoside

Base Information

Chemical Name:tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(tert-butoxycarbonyl)methyl]-α-D-glucopyranoside
CAS No.:1124225-87-1
Molecular Formula:C₃₇H₄₈O₇
Molecular Weight:604.784
Hs Code.:

Synonyms:tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(tert-butoxycarbonyl)methyl]-α-D-glucopyranoside

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Chemical Property of tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(tert-butoxycarbonyl)methyl]-α-D-glucopyranoside

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Technology Process of tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(tert-butoxycarbonyl)methyl]-α-D-glucopyranoside

There total 3 articles about tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(tert-butoxycarbonyl)methyl]-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: 65.0%

: 1124225-72-4
(3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran

: 75-65-0
tert-butyl alcohol

: 1124225-87-1
tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(tert-butoxycarbonyl)methyl]-α-D-glucopyranoside

Guidance literature:: (3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran; With calcium sulfate; scandium tris(trifluoromethanesulfonate); In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

tert-butyl alcohol; In dichloromethane; at 0 - 20 ℃; stereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.200802178

Reference yield:

: 946512-97-6
methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(bis-methoxycarbonyl)methyl]-β-D-glucopyranoside

: 1124225-87-1
tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(tert-butoxycarbonyl)methyl]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate / methanol; water / 1 h / Inert atmosphere; Reflux

2.1: acetic acid / toluene / 1 h / 110 °C / pH 3 - 4 / Inert atmosphere

3.1: calcium sulfate; scandium tris(trifluoromethanesulfonate) / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

With calcium sulfate; lithium hydroxide monohydrate; acetic acid; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2011.01.069

Reference yield:

: 1032716-06-5
methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(dicarboxy)methyl]-β-D-glucopyranoside

: 1124225-87-1
tert-butyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(tert-butoxycarbonyl)methyl]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: acetic acid / toluene / 1 h / 110 °C / pH 3 - 4 / Inert atmosphere

2.1: calcium sulfate; scandium tris(trifluoromethanesulfonate) / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

With calcium sulfate; acetic acid; scandium tris(trifluoromethanesulfonate); In dichloromethane; toluene;
DOI:10.1016/j.tet.2011.01.069