methyl (ethyl 2,3-di-O-benzyl-4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-thio-β-D-glucopyranosid)uronate

Base Information

Chemical Name:methyl (ethyl 2,3-di-O-benzyl-4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-thio-β-D-glucopyranosid)uronate
CAS No.:725228-98-8
Molecular Formula:C₄₅H₅₁N₃O₁₁S
Molecular Weight:841.979
Hs Code.:

Synonyms:methyl (ethyl 2,3-di-O-benzyl-4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-thio-β-D-glucopyranosid)uronate

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Chemical Property of methyl (ethyl 2,3-di-O-benzyl-4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-thio-β-D-glucopyranosid)uronate

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Technology Process of methyl (ethyl 2,3-di-O-benzyl-4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-thio-β-D-glucopyranosid)uronate

There total 3 articles about methyl (ethyl 2,3-di-O-benzyl-4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-thio-β-D-glucopyranosid)uronate 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: 67.0%

: 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α/β-D-glucopyranose

: 725228-67-1
methyl (ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranosid)uronate

: 725228-98-8
methyl (ethyl 2,3-di-O-benzyl-4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-thio-β-D-glucopyranosid)uronate

Guidance literature:: With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 3 A molecular sieve; 2,4,5-tri-tert-butylpyrimidine; In dichloromethane; at -40 - 0 ℃;
DOI:10.1021/ol049380+

Reference yield:

: 152964-70-0
ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

: 725228-98-8
methyl (ethyl 2,3-di-O-benzyl-4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-thio-β-D-glucopyranosid)uronate

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / 2,2,6,6-tetramethyl-1-piperidinyloxyl; [bis(acetoxy)iodo]benzene / CH₂Cl₂; H₂O / 0.75 h / 20 °C

2: 92 percent / dimethylformamide; diethyl ether / 20 °C

3: 67 percent / Ph₂SO; Tf₂O; 3 Angstroem molecular sieves / tri-tert-butylpyrimidine / CH₂Cl₂ / -40 - 0 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trifluoromethylsulfonic anhydride; [bis(acetoxy)iodo]benzene; 1,1'-sulfinylbisbenzene; 3 A molecular sieve; 2,4,5-tri-tert-butylpyrimidine; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol049380+

Reference yield:

: 725228-66-0
ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranosiduronic acid

: 725228-98-8
methyl (ethyl 2,3-di-O-benzyl-4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-thio-β-D-glucopyranosid)uronate

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / dimethylformamide; diethyl ether / 20 °C

2: 67 percent / Ph₂SO; Tf₂O; 3 Angstroem molecular sieves / tri-tert-butylpyrimidine / CH₂Cl₂ / -40 - 0 °C

With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 3 A molecular sieve; 2,4,5-tri-tert-butylpyrimidine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol049380+