1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol

Base Information

• Chemical Name: 1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol
• CAS No.: 156160-19-9
• Molecular Formula: C₄₈H₅₈N₂O₁₁
• Molecular Weight: 838.995
• Mol file: 156160-19-9.mol

Synonyms:1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol

Chemical Property of 1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol

There total 2 articles about 1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol 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: 78.6%

p-pivalolaminobenzyl 2,2,2-trichloroacetimidate (137105-38-5) + 1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-α-D-glucopyranosyl>-sn-glycerol (156160-17-7) → 1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol (156160-19-9)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at -70 ℃; for 2h;

DOI:10.1246/bcsj.67.473

Reference yield:

1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(2,2,2-trichloroethoxycarbonyl)-α,β-D-glucopyranosyl>-sn-glycerol → 1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol (156160-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 74.2 percent / 0.1M NaOMe / 12 h / 0 °C

2: 78.6 percent / triflic acid / CH₂Cl₂ / 2 h / -70 °C

With trifluorormethanesulfonic acid; sodium methylate; In dichloromethane;

DOI:10.1246/bcsj.67.473

Reference yield:

1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol (156160-19-9) → N-{4-[(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-{(R)-2,3-bis-[((E)-propenyl)oxy]-propoxy}-5-(4-nitro-benzyloxy)-tetrahydro-pyran-2-ylmethoxymethyl]-phenyl}-2,2-dimethyl-propionamide

Guidance literature:

With (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; hydrogen; In tetrahydrofuran; for 0.00833333h; Ambient temperature;

DOI:10.1246/bcsj.67.473

upstream raw materials:

p-pivalolaminobenzyl 2,2,2-trichloroacetimidate

1,2-di-O-allyl-3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-α-D-glucopyranosyl>-sn-glycerol

Downstream raw materials:

3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol

3-O-<3,4-di-O-benzyl-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-1,2-di-O-palmitoyl-sn-glycerol

3-O-<2-O-(p-aminobenzyl)-3,4-di-O-benzyl-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-1,2-di-O-palmitoyl-sn-glycerol