α-D-Mannopyranoside, phenyl 2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-

Base Information

• Chemical Name: α-D-Mannopyranoside, phenyl 2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-
• CAS No.: 159407-17-7
• Molecular Formula: C33H32O5S
• Molecular Weight: 540.68
• Mol file: 159407-17-7.mol

Synonyms:Phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-Mannopyranoside;α-D-Mannopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-;a-D-Mannopyranoside, phenyl 2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-;α-D-Mannopyranoside, phenyl 2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-;2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-α-D--pyranose phenyl phenyl ester;2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-α-D--pyranose phenyl phenyl ester

Chemical Property of α-D-Mannopyranoside, phenyl 2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-

Chemical Property:

• Boiling Point: 675.3±55.0 °C(Predicted)
• PSA: 71.45000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 6.78860

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of α-D-Mannopyranoside, phenyl 2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-

There total 14 articles about α-D-Mannopyranoside, phenyl 2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio- 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: 98.0%

benzyl bromide (100-39-0) + phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-17-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; paraffin; for 8h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00360-8

Reference yield: 88.0%

benzaldehyde dimethyl acetal (1125-88-8) + phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside (449761-78-8) → phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-17-7)

Guidance literature:

With iron(III) chloride; In acetonitrile; at 20 ℃; for 2.5h;

DOI:10.1016/j.carres.2011.01.003

Reference yield: 31.0%

methyl 2,3-di-O-benzyl-6-O-acetyl-α-D-glucopyranoside (20771-21-5,51842-23-0,51842-24-1,117561-20-3,125884-32-4,51842-22-9) + S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-α-D-mannopyranoside sulfoxide → methyl 6-O-acetyl-2,3-di-O-benzyl-4-O-(S-phenylsulfinyl)-α-D-glucopyranoside + methyl 6-O-acetyl-2,3-di-O-benzyl-4-O-(R-phenylsulfinyl)-α-D-glucopyranoside + methyl 6-O-acetyl-2,3-di-O-benzyl-4-O-[2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl]-α-D-glucopyranoside (1040282-43-6) + methyl-6-O-acetyl-2,3-di-O-benzyl-4-O-[2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl]-α-D-glucopyranoside (1040282-42-5) + phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-17-7)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 - 20 ℃; Molecular sieve;

DOI:10.1002/chem.200701864

upstream raw materials:

benzyl bromide

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

benzaldehyde dimethyl acetal

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

Downstream raw materials:

3-benzyloxy-2,2-dihexadecyloxymethylpropyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-mannopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranoside

C₅₅H₅₆O₁₂

3-benzyloxy-2,2-dihexadecyloxymethylpropyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-mannopyranoside

2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-α-D-mannopyranoside