(1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

Base Information

• Chemical Name: (1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol
• CAS No.: 1163143-63-2
• Molecular Formula: C₂₀H₂₃NO₄S
• Molecular Weight: 373.473
• Mol file: 1163143-63-2.mol

Synonyms:(1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

Chemical Property of (1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

There total 1 articles about (1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol 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: 90.0%

(1S,5S,6S,8S)-2-benzyl-8-hydroxymethyl-6-phenylthio-3,7-dioxa-2-azabicyclo[3.3.1]-nonan-9-one (1163143-60-9) → (1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol (1163143-63-2)

Guidance literature:

(1S,5S,6S,8S)-2-benzyl-8-hydroxymethyl-6-phenylthio-3,7-dioxa-2-azabicyclo[3.3.1]-nonan-9-one; With sodium tetrahydroborate; ethanol; at -40 ℃; for 3h; Inert atmosphere;

With water; In dichloromethane;

DOI:10.1002/anie.200805724

Reference yield: 99.0%

(1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol (1163143-63-2) + acetic anhydride (108-24-7) → [(1R,5S,6S,8S,9R)-9-acetoxy-2-benzyl-6-phenylthio-3,7-dioxa-2-azabicyclo[3.3.1]nonan-8-yl]methyl acetate

Guidance literature:

With pyridine; dmap; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201001060

Reference yield: 96.0%

methanol (67-56-1) + (1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol (1163143-63-2) → (1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-methoxy-3,7-dioxa-2-aza-bicyclo[3.3.1]-nonan-9-ol (1163143-66-5)

Guidance literature:

methanol; (1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-phenylsulfanyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol; With N-Bromosuccinimide; at 20 ℃; for 0.5h; Inert atmosphere;

With water; sodium hydrogencarbonate;

DOI:10.1002/anie.200805724

upstream raw materials:

(1S,5S,6S,8S)-2-benzyl-8-hydroxymethyl-6-phenylthio-3,7-dioxa-2-azabicyclo[3.3.1]-nonan-9-one

Downstream raw materials:

(1R,5S,6S,8S,9R)-2-benzyl-8-hydroxymethyl-6-methoxy-3,7-dioxa-2-aza-bicyclo[3.3.1]-nonan-9-ol

phenyl 1-thio-4-benzylamino-2,4-dideoxy-2-hydroxymethyl-D-talopyranoside