Phenyl 4,6-O-Benzylidene-1-thio-a-D-mannopyranoside

Base Information

• Chemical Name: Phenyl 4,6-O-Benzylidene-1-thio-a-D-mannopyranoside
• CAS No.: 159407-19-9
• Molecular Formula: C19H20 O5 S
• Molecular Weight: 360.431
• Mol file: 159407-19-9.mol

Synonyms:a-D-Mannopyranoside, phenyl4,6-O-(phenylmethylene)-1-thio-, (R)-; Pyrano[3,2-d]-1,3-dioxin, a-D-mannopyranoside deriv.

Chemical Property of Phenyl 4,6-O-Benzylidene-1-thio-a-D-mannopyranoside

Chemical Property:

• PSA: 93.45000
• LogP: 2.33960
• Storage Temp.: 2-8°C
• Solubility.: Chloroform

Purity/Quality:

98%,99%, ^*data from raw suppliers

Phenyl4,6-O-Benzylidene-1-thio-α-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Phenyl 4,6-O-Benzylidene-1-thio-α-D-mannopyranoside (cas# 159407-19-9) is a compound useful in organic synthesis.

Technology Process of Phenyl 4,6-O-Benzylidene-1-thio-a-D-mannopyranoside

There total 15 articles about Phenyl 4,6-O-Benzylidene-1-thio-a-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: 94.0%

benzaldehyde dimethyl acetal (1125-88-8) + (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 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9)

Guidance literature:

With (1S)-10-camphorsulfonic acid; In acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/chem.201304950

Reference yield: 55.0%

phenyl 1-thio-D-mannopyranoside (151763-69-8) + benzaldehyde dimethyl acetal (1125-88-8) → phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.0c00402

Reference yield: 51.0%

benzaldehyde dimethyl acetal (1125-88-8) + (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) → C26H24O5S + phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; for 2h; under 150.015 Torr;

DOI:10.1055/s-0028-1083283

upstream raw materials:

benzaldehyde dimethyl acetal

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

phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside

D-Mannose pentaacetate

Downstream raw materials:

phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside

S-phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside

S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside