phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

Base Information

• Chemical Name: phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside
• CAS No.: 868258-63-3
• Molecular Formula: C₂₆H₂₆O₅S
• Molecular Weight: 450.555
• Mol file: 868258-63-3.mol

Synonyms:phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

Chemical Property of phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

There total 4 articles about phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside 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: 91.0%

phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside (868258-62-2) + benzoyl chloride (98-88-4) → phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside (868258-63-3)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -50 - -10 ℃;

DOI:10.1021/jm050368c

Reference yield:

phenyl 2-O-benzyl-1-thio-β-D-fucopyranoside (868258-60-0) → phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside (868258-63-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: CH₂Cl₂

3: 90 percent / MeONa / methanol / 2 h / 20 °C

4: 91 percent / DMAP; DIPEA / CH₂Cl₂ / -50 - -10 °C

With pyridine; dmap; sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/jm050368c

Reference yield:

phenyl 3,4-di-O-acetyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside (868258-61-1) → phenyl 4-O-benzoyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside (868258-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / MeONa / methanol / 2 h / 20 °C

2: 91 percent / DMAP; DIPEA / CH₂Cl₂ / -50 - -10 °C

With dmap; sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/jm050368c

upstream raw materials:

phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

benzoyl chloride

phenyl 2-O-benzyl-1-thio-β-D-fucopyranoside

phenyl 3,4-di-O-acetyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside

Downstream raw materials:

phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside

6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

6-O-(3-amino-3,6-dideoxy-α-D-glucopyranosyl)neamine