phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside
• CAS No.: 150935-64-1
• Molecular Formula: C₃₉H₄₂O₈SSi
• Molecular Weight: 698.909

Synonyms:phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

There total 4 articles about phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside 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:

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5) → phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside (150935-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 8.1 g / NaOCH₃ / methanol

2: 1.) pyridine, 2.) pyridine / 1.) r.t., overnight, 2.) CH₂Cl₂, toluene, 24 h

With pyridine; sodium methylate; In methanol;

Reference yield:

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0) → phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside (150935-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 2 h / Ambient temperature

2: pyridine / 4 h / Ambient temperature

With pyridine;

DOI:10.1016/S0040-4020(01)80165-4

Reference yield:

benzoyl chloride (98-88-4) + phenyl 6-O-(tert-butyldimethylsilyloxy)-1-thio-α-D-mannopyranoside (152488-25-0) → phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside (150935-64-1)

Guidance literature:

With pyridine; for 4h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80165-4

upstream raw materials:

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

benzoyl chloride

tert-butyldimethylsilyl chloride

phenyl 6-O-(tert-butyldimethylsilyloxy)-1-thio-α-D-mannopyranoside

Downstream raw materials:

phenyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-phosphate-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

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