(+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Base Information

• Chemical Name: (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• CAS No.: 305791-05-3
• Molecular Formula: C₅₈H₁₁₆O₉Si₅
• Molecular Weight: 1097.98
• Mol file: 305791-05-3.mol

Synonyms:(+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Chemical Property of (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside

There total 12 articles about (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-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: 83.0%

phenyllithium (591-51-5) + ((5S,6S)-2,2-dimethyl-5-methoxymethoxy-3-tridecyl-5,6-dihydro-2H-1,2-oxasilin-6-yl)methyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside (305791-03-1) → (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside (305791-05-3)

Guidance literature:

In tetrahydrofuran; diethyl ether; cyclohexane; at 0 - 20 ℃; for 18h;

DOI:10.1021/jo000690p

Reference yield:

allyl β-D-glucopyranoside (2595-07-5,7464-56-4,34384-79-7,41308-76-3,48149-72-0,48149-74-2,85249-43-0,119479-69-5,821794-45-0) → (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside (305791-05-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 40 °C

2.1: O₃; Sudan red / ethanol / 0.17 h / -78 °C

2.2: 85 percent / Me₂S / ethanol / -78 - 20 °C

3.1: cyclohexane; tetrahydrofuran / 18 h / -85 °C

4.1: 1.3 g / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

5.1: 70 percent / [(CF₃)2MeCO]2Mo(=CHCMe₂Ph)(=NC₆H₃-2,6-i-Pr₂) / heptane / 24 h / 45 °C

6.1: 83 percent / cyclohexane; diethyl ether; tetrahydrofuran / 18 h / 0 - 20 °C

With 2,6-dimethylpyridine; bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum; sudan red; ozone; In tetrahydrofuran; diethyl ether; ethanol; n-heptane; dichloromethane; cyclohexane; 1.1: Condensation / 2.1: ozonolysis / 2.2: Reduction / 3.1: Addition / 4.1: Etherification / 5.1: ring closing metathesis / 6.1: Ring cleavage;

DOI:10.1021/jo000690p

Reference yield:

pentadec-1-yne (765-13-9) → (+)-1-O-[(2S,3S,4Z)-2-hydroxy-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside (305791-05-3)

Guidance literature:

Multi-step reaction with 7 steps

1: CH₂Cl₂ / 3.5 h / 0 °C

2: 5.24 g / AcOH / CH₂Cl₂ / 1 h / 0 °C

3: 67 percent / t-BuLi / tetrahydrofuran; pentane / 3.5 h / -78 - 20 °C

4: CH₂Cl₂ / 0.33 h / 20 °C

5: 1.3 g / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

6: 70 percent / [(CF₃)2MeCO]2Mo(=CHCMe₂Ph)(=NC₆H₃-2,6-i-Pr₂) / heptane / 24 h / 45 °C

7: 83 percent / cyclohexane; diethyl ether; tetrahydrofuran / 18 h / 0 - 20 °C

With 2,6-dimethylpyridine; bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum; tert.-butyl lithium; acetic acid; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; cyclohexane; pentane; 1: Addition / 2: Substitution / 3: Substitution / 4: Substitution / 5: Etherification / 6: ring closing metathesis / 7: Ring cleavage;

DOI:10.1021/jo000690p

upstream raw materials:

phenyllithium

((5S,6S)-2,2-dimethyl-5-methoxymethoxy-3-tridecyl-5,6-dihydro-2H-1,2-oxasilin-6-yl)methyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside

allyl β-D-glucopyranoside

pentadec-1-yne

Downstream raw materials:

(+)-1-O-[(2R,3S,4Z)-2-azido-3-methoxymethoxy-5-dimethylphenylsilyl-octadec-4-en-1-yl] 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside