phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside
• CAS No.: 111425-50-4
• Molecular Formula: C₁₅H₁₈O₃S
• Molecular Weight: 278.372
• Mol file: 111425-50-4.mol

Synonyms:phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside

Chemical Property of phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside

There total 6 articles about phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside 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: 85.0%

2-Methoxypropene (116-11-0) + thiophenyl 2,3-dideoxy-α-D-glucopyranoside (111425-52-6) → phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside (111425-50-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 23 ℃; for 3h;

DOI:10.1021/ol0069002

Reference yield:

phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside (111425-49-1,125848-19-3,137740-45-5,111425-48-0,286410-13-7) → phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside (111425-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1: LiOH / methanol / 1 h / 20 °C

2: CSA / dimethylformamide / 1 h / 20 °C

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

DOI:10.1016/S0022-328X(00)00920-7

Reference yield:

thiophenol (108-98-5) → phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside (111425-50-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / SnCl₄ / CH₂Cl₂ / 0.42 h / -20 °C

2: 98 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1.25 h / 0 °C

3: 85 percent / pyridinium-p-toluenesulfonate / CH₂Cl₂ / 3 h / 23 °C

With pyridinium p-toluenesulfonate; tin(IV) chloride; potassium carbonate; In methanol; dichloromethane; 1: Ferrier substitution;

DOI:10.1021/ol0069002

upstream raw materials:

methylallylether

thiophenyl 2,3-dideoxy-α-D-glucopyranoside

2-Methoxypropene

phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside