methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside
• CAS No.: 938082-00-9
• Molecular Formula: C₃₇H₅₂O₁₃Si
• Molecular Weight: 732.898
• Mol file: 938082-00-9.mol

Synonyms:methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside

Chemical Property of methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside

There total 5 articles about methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-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: 99.0%

methyl 6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside (938081-97-1) + 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (113893-72-4) → methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside (938082-00-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol070496q

Reference yield:

methyl 6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-xylo-hexopyranosid-4-ulose (938081-98-2) → methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside (938082-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 297 mg / NaBH₄ / ethanol; H₂O / 1 h / 20 °C

2: 99 percent / molecular sieves 3 Angstroem; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; In ethanol; dichloromethane; water;

DOI:10.1021/ol070496q

Reference yield:

2,3,4-tri-O-acetyl-L-rhamnopyranose (28915-80-2,40591-53-5,40591-54-6,40591-55-7,120449-19-6,120449-20-9,143332-42-7,148081-39-4,151413-57-9,151413-58-0) → methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->4)-6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside (938082-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / NaH / CH₂Cl₂ / 1 h / 20 °C

2: 99 percent / molecular sieves 3 Angstroem; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium hydride; In dichloromethane;

DOI:10.1021/ol070496q

upstream raw materials:

methyl 6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-glucopyranoside

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

methyl 6-O-[tert-butyl(diphenyl)silyl]-2,3-di-O-methyl-α-D-xylo-hexopyranosid-4-ulose

2,3,4-tri-O-acetyl-L-rhamnopyranose