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

Base Information

• Chemical Name: 3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol
• CAS No.: 156160-20-2
• Molecular Formula: C₄₂H₅₀N₂O₁₁
• Molecular Weight: 758.866
• Mol file: 156160-20-2.mol

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

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

There total 5 articles about 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:

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 → 3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol (156160-20-2)

Guidance literature:

With acetic acid; at 70 ℃; for 3h; Yield given;

DOI:10.1246/bcsj.67.473

Reference yield:

p-pivalolaminobenzyl 2,2,2-trichloroacetimidate (137105-38-5) → 3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol (156160-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 78.6 percent / triflic acid / CH₂Cl₂ / 2 h / -70 °C

2: 6H₅)2)2>PF₆, H₂ / tetrahydrofuran / 0.01 h / Ambient temperature

3: 90percent aq. acetic acid / 3 h / 70 °C

With (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trifluorormethanesulfonic acid; hydrogen; acetic acid; In tetrahydrofuran; 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-(2,2,2-trichloroethoxycarbonyl)-α,β-D-glucopyranosyl>-sn-glycerol → 3-O-<3,4-di-O-benzyl-2-O-(p-nitrobenzyl)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol (156160-20-2)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 6H₅)2)2>PF₆, H₂ / tetrahydrofuran / 0.01 h / Ambient temperature

4: 90percent aq. acetic acid / 3 h / 70 °C

With (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trifluorormethanesulfonic acid; hydrogen; sodium methylate; acetic acid; In tetrahydrofuran; dichloromethane;

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)-6-O-(p-pivaloylaminobenzyl)-α-D-glucopyranosyl>-sn-glycerol

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

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