ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside
CAS No.:151992-77-7
Molecular Formula:C₃₅H₄₃N₃O₁₃S
Molecular Weight:745.805
Hs Code.:

Synonyms:ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside

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Chemical Property of ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside

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Technology Process of ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside

There total 5 articles about ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-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: 60.0%

: methyl (2,3,4-tri-O-acetyl-β-L-idopyranosyl bromide)uronate

: 151992-76-6
Ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

: 151992-77-7
ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -15 ℃; for 0.25h;
DOI:10.1016/0008-6215(93)84030-A

Reference yield:

: 152141-82-7
2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl nitrate

: 151992-77-7
ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 73 percent / Et₄NCl / acetonitrile / 5 h / Ambient temperature

2: 52 percent / dimethylformamide / 1 h / Ambient temperature

3: 1) NaOMe / 1) MeOH, r.t., 30 min

4: 83 percent / NaCNBH₃, HCl, molecular sieves / tetrahydrofuran / 0.17 h

5: 60 percent / silver triflate, 2,6-di-tert-butyl-4-methylpyridine, molecular sieves / CH₂Cl₂ / 0.25 h / -15 °C

With hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; tetraethylammonium chloride; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(93)84030-A

Reference yield:

: 151992-73-3
2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl chloride

: 151992-77-7
ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 52 percent / dimethylformamide / 1 h / Ambient temperature

2: 1) NaOMe / 1) MeOH, r.t., 30 min

3: 83 percent / NaCNBH₃, HCl, molecular sieves / tetrahydrofuran / 0.17 h

4: 60 percent / silver triflate, 2,6-di-tert-butyl-4-methylpyridine, molecular sieves / CH₂Cl₂ / 0.25 h / -15 °C

With hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(93)84030-A