allyl [4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

Chemical Name:allyl [4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
CAS No.:628281-07-2
Molecular Formula:C₃₇H₄₃N₃O₁₁
Molecular Weight:705.762
Hs Code.:

Synonyms:allyl [4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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Chemical Property of allyl [4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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Technology Process of allyl [4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 6 articles about allyl [4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(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: 89.0%

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 628281-06-1
allyl β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

: 628281-07-2
allyl [4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: With camphor-10-sulfonic acid; In acetonitrile; at 20 ℃; for 1h;
DOI:10.1002/ejoc.200300254

Reference yield:

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

: 628281-07-2
allyl [4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

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

2: 99 percent / NaH / dimethylformamide / 0.58 h / 0 °C

3: 90 percent / NaBH₃CN; HCl; 4A MS / methyl orange / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

4: 4A MS; silver triflate / CH₂Cl₂ / 2.5 h / -40 °C

5: 10.9 g / MeONa / methanol

6: 89 percent / camphorsulfonic acid / acetonitrile / 1 h / 20 °C

With hydrogenchloride; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; methyl orange; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200300254

Reference yield:

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

: 628281-07-2
allyl [4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / NaH / dimethylformamide / 0.58 h / 0 °C

2: 90 percent / NaBH₃CN; HCl; 4A MS / methyl orange / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

3: 4A MS; silver triflate / CH₂Cl₂ / 2.5 h / -40 °C

4: 10.9 g / MeONa / methanol

5: 89 percent / camphorsulfonic acid / acetonitrile / 1 h / 20 °C

With hydrogenchloride; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; methyl orange; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200300254