methyl (4,6-O-benzylidene-2-O-diazoacetyl-3-O-pivaloyl-β-D-glucopyranoside)-(1->6)-2,3,4-O-methyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl (4,6-O-benzylidene-2-O-diazoacetyl-3-O-pivaloyl-β-D-glucopyranoside)-(1->6)-2,3,4-O-methyl-α-D-glucopyranoside
CAS No.:1256138-33-6
Molecular Formula:C₃₀H₄₂N₂O₁₃
Molecular Weight:638.669
Hs Code.:

Synonyms:methyl (4,6-O-benzylidene-2-O-diazoacetyl-3-O-pivaloyl-β-D-glucopyranoside)-(1->6)-2,3,4-O-methyl-α-D-glucopyranoside

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Chemical Property of methyl (4,6-O-benzylidene-2-O-diazoacetyl-3-O-pivaloyl-β-D-glucopyranoside)-(1->6)-2,3,4-O-methyl-α-D-glucopyranoside

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Technology Process of methyl (4,6-O-benzylidene-2-O-diazoacetyl-3-O-pivaloyl-β-D-glucopyranoside)-(1->6)-2,3,4-O-methyl-α-D-glucopyranoside

There total 4 articles about methyl (4,6-O-benzylidene-2-O-diazoacetyl-3-O-pivaloyl-β-D-glucopyranoside)-(1->6)-2,3,4-O-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: 43.0%

: 1256138-11-0
phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-pivaloyl-1-thio-β-D-glucopyranoside

: 1256138-33-6
methyl (4,6-O-benzylidene-2-O-diazoacetyl-3-O-pivaloyl-β-D-glucopyranoside)-(1->6)-2,3,4-O-methyl-α-D-glucopyranoside

Guidance literature:: phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-pivaloyl-1-thio-β-D-glucopyranoside; With 2,4,6-tri-tertbutylpyridine; trifluorormethanesulfonic acid; 1,1'-sulfinylbisbenzene; In dichloromethane; at -70 ℃; for 2h; Inert atmosphere; Molecular sieve;

With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1021/ja1054065

Reference yield:

: 1256138-11-0
phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-pivaloyl-1-thio-β-D-glucopyranoside

: 4153-24-6
1,2,3,4-tetra-O-methyl-α-D-glucopyranose

: 1256138-33-6
methyl (4,6-O-benzylidene-2-O-diazoacetyl-3-O-pivaloyl-β-D-glucopyranoside)-(1->6)-2,3,4-O-methyl-α-D-glucopyranoside

: 1256138-40-5
C₃₀H₄₃BrO₁₃

Guidance literature:: phenyl 4,6-O-benzylidene-2-O-bromoacetyl-3-O-pivaloyl-1-thio-β-D-glucopyranoside; With 2,4,6-tri-tertbutylpyridine; 1,1'-sulfinylbisbenzene; In dichloromethane; at 20 ℃; for 1h; Molecular sieve; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; at -20 ℃; for 0.166667h; Inert atmosphere;

1,2,3,4-tetra-O-methyl-α-D-glucopyranose; Further stages;
DOI:10.1002/chem.201203725

Reference yield:

: 6984-43-6
(2S,3R,4S,5R,6R)-2,3,4,5-tetramethoxy-6-((trityloxy)methyl)tetrahydro-2H-pyran

: 1256138-33-6
methyl (4,6-O-benzylidene-2-O-diazoacetyl-3-O-pivaloyl-β-D-glucopyranoside)-(1->6)-2,3,4-O-methyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: water; acetic acid / 4 h / 40 °C

2.1: 1,1'-sulfinylbisbenzene; 2,4,6-tri-tertbutylpyridine / dichloromethane / 1 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 0.17 h / -20 °C / Inert atmosphere

With 2,4,6-tri-tertbutylpyridine; 1,1'-sulfinylbisbenzene; water; acetic acid; In dichloromethane;
DOI:10.1002/chem.201203725