allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

Chemical Name:allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
CAS No.:628281-04-9
Molecular Formula:C₃₉H₄₅N₃O₁₂
Molecular Weight:747.799
Hs Code.:

Synonyms:allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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

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

There total 17 articles about allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-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: 70.0%

: 75-36-5
acetyl chloride

: 628281-02-7
allyl (methyl 3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

: Acetic acid (1R,3R,4R,7S,8S)-3-((2R,3S,4R,5R,6S)-6-allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-8-benzyloxy-6-oxo-2,5-dioxa-bicyclo[2.2.2]oct-7-yl ester

: (2R,3S,4R,5R,6R)-3-Acetoxy-6-((2R,3S,4R,5R,6S)-6-allyloxy-5-azido-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 628281-04-9
allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

: 628281-00-5
allyl (methyl 2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: allyl (methyl 3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside; With di(n-butyl)tin oxide; In benzene; at 90 ℃; for 0.5h;

acetyl chloride; With triethylamine; at 20 ℃; for 1h; pH=8;
DOI:10.1002/ejoc.200300254

Reference yield:

: 152432-87-6
allyl 2-azido-2-deoxy-α-D-glucopyranoside

: 628281-04-9
allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: (+/-)-camphorsulfonic acid / acetonitrile / 8 h

2.1: 99 percent / NaH / dimethylformamide / 0.58 h / 0 °C

3.1: 90 percent / NaBH₃CN; HCl; 4A MS / methyl orange / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

4.1: 81 percent / 4A MS; AgOTf / CH₂Cl₂ / 0 °C

5.1: 90 percent / K₂CO₃ / methanol / 20 °C

6.1: Bu₂SnO / benzene / 0.5 h / 90 °C

6.2: 70 percent / Et₃N / 1 h / 20 °C / pH 8

With hydrogenchloride; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; potassium carbonate; methyl orange; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1002/ejoc.200300254

Reference yield:

: 628280-97-7
allyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

: 628281-04-9
allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / NaH / dimethylformamide / 0.58 h / 0 °C

2.1: 90 percent / NaBH₃CN; HCl; 4A MS / methyl orange / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

3.1: 81 percent / 4A MS; AgOTf / CH₂Cl₂ / 0 °C

4.1: 90 percent / K₂CO₃ / methanol / 20 °C

5.1: Bu₂SnO / benzene / 0.5 h / 90 °C

5.2: 70 percent / Et₃N / 1 h / 20 °C / pH 8

With hydrogenchloride; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; potassium carbonate; methyl orange; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1002/ejoc.200300254