(3aR,4S,5aR,9aS,9bR)-8-Phenyl-4-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-2-one

Base Information

• Chemical Name: (3aR,4S,5aR,9aS,9bR)-8-Phenyl-4-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-2-one
• CAS No.: 371123-25-0
• Molecular Formula: C₂₀H₁₉NO₅S
• Molecular Weight: 385.441
• Mol file: 371123-25-0.mol

Synonyms:(3aR,4S,5aR,9aS,9bR)-8-Phenyl-4-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-2-one

Chemical Property of (3aR,4S,5aR,9aS,9bR)-8-Phenyl-4-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-2-one

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,5aR,9aS,9bR)-8-Phenyl-4-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-2-one

There total 2 articles about (3aR,4S,5aR,9aS,9bR)-8-Phenyl-4-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-2-one 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%

benzaldehyde dimethyl acetal (1125-88-8) + (3aR,4S,6R,7S,7aR)-7-Hydroxy-6-hydroxymethyl-4-phenylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one (371123-23-8) → (3aR,4S,5aR,9aS,9bR)-8-Phenyl-4-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-2-one (371123-25-0)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1021/ja0162109

Reference yield:

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside (371123-22-7) → (3aR,4S,5aR,9aS,9bR)-8-Phenyl-4-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-2-one (371123-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CSA / dimethylformamide / 60 °C

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/ja0162109

Reference yield: 98.0%

(3aR,4S,5aR,9aS,9bR)-8-Phenyl-4-phenylsulfanyl-hexahydro-1,5,7,9-tetraoxa-3-aza-cyclopenta[a]naphthalen-2-one (371123-25-0) → (3aR,4S,6R,7S,7aR)-6-Benzyloxymethyl-7-hydroxy-4-phenylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one (371123-29-4)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja0162109

upstream raw materials:

benzaldehyde dimethyl acetal

(3aR,4S,6R,7S,7aR)-7-Hydroxy-6-hydroxymethyl-4-phenylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside

Downstream raw materials:

(3aR,4S,6R,7S,7aR)-6-Benzyloxymethyl-7-hydroxy-4-phenylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one

Acetic acid (3aR,4S,6R,7R,7aR)-6-benzyloxymethyl-2-oxo-4-phenylsulfanyl-hexahydro-pyrano[3,4-d]oxazol-7-yl ester