benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside
• CAS No.: 1400879-04-0
• Molecular Formula: C₁₉H₂₄O₆S
• Molecular Weight: 380.462

Synonyms:benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside

Chemical Property of benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside

Chemical Property:

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Technology Process of benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside

There total 2 articles about benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-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: 82.0%

(RS/SS)-benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylsulfinyl)-α-D-arabino-hexopyranoside → benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside (1400879-04-0)

Guidance literature:

With pyridine; trifluoroacetic anhydride; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tet.2012.08.011

Reference yield:

benzyl 4,6-di-O-acetyl-2,3-dideoxy-3-ethylthio-α-D-arabino-hexopyranoside (1320337-31-2) → benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside (1400879-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.67 h / -78 °C / Inert atmosphere

2: trifluoroacetic anhydride; pyridine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

With pyridine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In dichloromethane; 2: |Pummerer Sulfoxide Rearrangement;

DOI:10.1016/j.tet.2012.08.011

Reference yield: 92.0%

benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside (1400879-04-0) → (RS/SS)-benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylsulfinyl)-α-D-erythro-hex-2-enopyranoside

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1016/j.tet.2012.08.011

upstream raw materials:

benzyl 4,6-di-O-acetyl-2,3-dideoxy-3-ethylthio-α-D-arabino-hexopyranoside

Downstream raw materials:

(S_S)-benzyl 2-O-methyl-3-deoxy-(3-ethylsulfinyl)-α-D-manno-pyranoside

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