phenyl 1-thio-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside

Base Information

• Chemical Name: phenyl 1-thio-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside
• CAS No.: 331268-34-9
• Molecular Formula: C₄₁H₅₄O₄SSi₂
• Molecular Weight: 699.114

Synonyms:phenyl 1-thio-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside

Chemical Property of phenyl 1-thio-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside

Chemical Property:

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Technology Process of phenyl 1-thio-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside

There total 1 articles about phenyl 1-thio-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside 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%

phenylthiotrimethylsilane (4551-15-9) + 1-O-allyl-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside (239802-98-3) → phenyl 1-thio-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside (331268-34-9)

Guidance literature:

With zinc(II) iodide; In 1,2-dichloro-ethane; at 50 ℃; for 2h;

DOI:10.1246/cl.2000.432

Reference yield:

methanol (67-56-1) + phenyl 1-thio-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside (331268-34-9) → (2S,3R,4S,5S,6S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran + (2R,3R,4S,5S,6S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran

Guidance literature:

With N-Bromosuccinimide; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1246/cl.2000.432

Reference yield:

isopropyl alcohol (67-63-0,8013-70-5) + phenyl 1-thio-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside (331268-34-9) → (2R,3R,4S,5S,6S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-isopropoxy-6-methyl-tetrahydro-pyran + (2S,3R,4S,5S,6S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-isopropoxy-6-methyl-tetrahydro-pyran

Guidance literature:

With N-Bromosuccinimide; 4 A molecular sieve; In acetonitrile; at 0 ℃; for 0.166667h;

DOI:10.1246/cl.2000.432

upstream raw materials:

phenylthiotrimethylsilane

1-O-allyl-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-4-O-(tert-butyldiphenylsilyl)-α-L-rhamnopyranoside

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