methyl 2,3,4-tri-O-benzyl-6,7,9-trideoxy-8-S-phenyl-8-thio-α-D-gluco-non-8-enopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-6,7,9-trideoxy-8-S-phenyl-8-thio-α-D-gluco-non-8-enopyranoside
• CAS No.: 494212-15-6
• Molecular Formula: C₃₇H₄₀O₅S
• Molecular Weight: 596.788
• Mol file: 494212-15-6.mol

Synonyms:methyl 2,3,4-tri-O-benzyl-6,7,9-trideoxy-8-S-phenyl-8-thio-α-D-gluco-non-8-enopyranoside

Chemical Property of methyl 2,3,4-tri-O-benzyl-6,7,9-trideoxy-8-S-phenyl-8-thio-α-D-gluco-non-8-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-benzyl-6,7,9-trideoxy-8-S-phenyl-8-thio-α-D-gluco-non-8-enopyranoside

There total 2 articles about methyl 2,3,4-tri-O-benzyl-6,7,9-trideoxy-8-S-phenyl-8-thio-α-D-gluco-non-8-enopyranoside 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:

(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran (127214-37-3) → methyl 2,3,4-tri-O-benzyl-6,7,9-trideoxy-8-S-phenyl-8-thio-α-D-gluco-non-8-enopyranoside (494212-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 4 h / 0 - 23 °C

2: 156 mg / aqueous NaOH; tetrakis(triphenylphosphino)palladium / tetrahydrofuran; benzene / 4 h / Heating

With sodium hydroxide; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; benzene; 2: Suzuki cross-coupling;

DOI:10.1021/jo026163i

Reference yield:

phenyl α-bromovinyl sulfide (80485-53-6) + (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-[2-(9-bora-bicyclo[3.3.1]non-9-yl)-ethyl]-6-methoxy-tetrahydro-pyran → methyl 2,3,4-tri-O-benzyl-6,7,9-trideoxy-8-S-phenyl-8-thio-α-D-gluco-non-8-enopyranoside (494212-15-6)

Guidance literature:

With sodium hydroxide; tetrakis-(triphenylphosphino)-palladium⁽⁰⁾; In tetrahydrofuran; benzene; for 4h; Heating;

DOI:10.1021/jo026163i

Reference yield: 71.0%

methyl 2,3,4-tri-O-benzyl-6,7,9-trideoxy-8-S-phenyl-8-thio-α-D-gluco-non-8-enopyranoside (494212-15-6) → 4-((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)butan-2-one

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 0 ℃; for 5h;

DOI:10.1021/jo026163i

upstream raw materials:

phenyl α-bromovinyl sulfide

(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran