Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-pyranoside

Base Information

• Chemical Name: Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-pyranoside
• CAS No.: 159404-16-7
• Molecular Formula: C₁₆H₂₀O₅S
• Molecular Weight: 324.398
• Mol file: 159404-16-7.mol

Synonyms:Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-pyranoside

Chemical Property of Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-pyranoside

There total 1 articles about Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-pyranoside 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:

phenylthiotrimethylsilane (4551-15-9) + methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside (23339-17-5) → Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-pyranoside (159404-16-7) + Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-β-D-erythro-pyranoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 25 ℃; for 10h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00089a034

Reference yield: 100.0%

Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-pyranoside (159404-16-7) → (2R,3S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:

With potassium carbonate; In methanol; at 25 ℃; for 1h;

DOI:10.1021/jo00089a034

Reference yield:

Phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-pyranoside (159404-16-7) → Phenyl 4,6-di-O-isopropylidene-2,3-dideoxy-1-thio-α-D-erythro-pyranoside (159404-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / K₂CO₃ / methanol / 1 h / 25 °C

2: 92 percent / POCl₃ / CH₂Cl₂ / 12 h / 25 °C

With potassium carbonate; trichlorophosphate; In methanol; dichloromethane;

DOI:10.1021/jo00089a034

upstream raw materials:

phenylthiotrimethylsilane

methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside

Downstream raw materials:

Phenyl 4,6-di-O-isopropylidene-2,3-dideoxy-1-thio-α-D-erythro-pyranoside

Phenyl 4,6-di-O-isopropylidene-2,3-dideoxy-1-sulfonyl-α-D-erythro-pyranoside