(4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine

Base Information

• Chemical Name: (4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine
• CAS No.: 449761-79-9
• Molecular Formula: C₃₂H₃₁BO₅S
• Molecular Weight: 538.472
• Mol file: 449761-79-9.mol

Synonyms:(4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine

Chemical Property of (4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine

There total 2 articles about (4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine 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: 72.0%

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside (449761-78-8) + phenylboronic acid (98-80-6) → (4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine (449761-79-9)

Guidance literature:

In pyridine; for 10h; Heating;

DOI:10.1021/ja011406u

Reference yield:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside → (4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine (449761-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / p-toluenesulfonic acid / methanol / 0.5 h / Heating

2: 72 percent / pyridine / 10 h / Heating

With toluene-4-sulfonic acid; In pyridine; methanol;

DOI:10.1021/ja011406u

Reference yield:

1-adamanthanol (768-95-6) + (4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine (449761-79-9) → (4aR,6S,7S,8S,8aR)-6-(Adamantan-1-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine

Guidance literature:

(4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3,2]dioxaborinine; With trifluoromethylsulfonic anhydride; sulfobromophthalein sodium; In dichloromethane; at -60 ℃; for 0.0833333h;

1-adamanthanol; In dichloromethane; at -60 - 20 ℃; Further stages.;

DOI:10.1021/ja011406u

upstream raw materials:

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

phenylboronic acid