phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-bis(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-bis(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranoside
• CAS No.: 150935-66-3
• Molecular Formula: C₃₇H₃₁Cl₆O₁₁PS
• Molecular Weight: 927.404
• Mol file: 150935-66-3.mol

Synonyms:phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-bis(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranoside

Chemical Property of phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-bis(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-bis(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranoside

There total 4 articles about phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-bis(2,2,2-trichloroethoxy)phosphoryl-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: 98.0%

bis-(2,2,2-trichloroethyl)phosphorochloridate (17672-53-6) + phenyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside (150935-65-2) → phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-bis(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranoside (150935-66-3)

Guidance literature:

With pyridine; In dichloromethane; 1.) -40 deg C, 1 h, 2.) -20 deg C, overnight;

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-1-thio-6-O-bis(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranoside (150935-66-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 8.1 g / NaOCH₃ / methanol

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

3: 93 percent / acetic acid / tetrahydrofuran; H₂O / 120 h / Ambient temperature

4: 98 percent / pyridine / CH₂Cl₂ / 1.) -40 deg C, 1 h, 2.) -20 deg C, overnight

With pyridine; sodium methylate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; water;

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-1-thio-6-O-bis(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranoside (150935-66-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 93 percent / acetic acid / tetrahydrofuran; H₂O / 120 h / Ambient temperature

3: 98 percent / pyridine / CH₂Cl₂ / 1.) -40 deg C, 1 h, 2.) -20 deg C, overnight

With pyridine; acetic acid; In tetrahydrofuran; dichloromethane; water;

upstream raw materials:

bis-(2,2,2-trichloroethyl)phosphorochloridate

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

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

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

Downstream raw materials:

phenyl 2,3,4-tri-O-benzoyl-1-thio-6-O-<2,3,4-tri-O-benzoyl-6-O-bis-(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranosyl>-α-D-mannopyranoside

C₅₈H₄₈BrCl₆O₁₉P

1,3,4,6-tetra-O-acetyl-2-O-<2,3,4-tri-O-benzoyl-6-O-bis-(2,2,2-trichloroethoxy)phosphoryl-α-D-mannopyranosyl>-β-D-mannopyranose

C₄₃H₄₂BrCl₆O₁₉P