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

Base Information

• Chemical Name: (3aR,4S,6R,7S,7aR)-7-Hydroxy-6-hydroxymethyl-4-phenylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one
• CAS No.: 371123-23-8
• Molecular Formula: C₁₃H₁₅NO₅S
• Molecular Weight: 297.332

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

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

Chemical Property:

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

There total 1 articles about (3aR,4S,6R,7S,7aR)-7-Hydroxy-6-hydroxymethyl-4-phenylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-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: 93.0%

phenyl chloroformate (1885-14-9) + phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside (371123-22-7) → (3aR,4S,6R,7S,7aR)-7-Hydroxy-6-hydroxymethyl-4-phenylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one (371123-23-8)

Guidance literature:

DOI:10.1021/ja0162109

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: 90.0%

acetic anhydride (108-24-7) + (3aR,4S,6R,7S,7aR)-7-Hydroxy-6-hydroxymethyl-4-phenylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one (371123-23-8) → Acetic acid (3aR,4S,6R,7S,7aR)-6-acetoxymethyl-2-oxo-4-phenylsulfanyl-hexahydro-pyrano[3,4-d]oxazol-7-yl ester (371123-24-9)

Guidance literature:

With pyridine;

DOI:10.1021/ja0162109

upstream raw materials:

phenyl chloroformate

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

Downstream raw materials:

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

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

(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

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