ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside

Base Information

• Chemical Name: ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside
• CAS No.: 347382-91-6
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321

Synonyms:ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside

Chemical Property of ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside

Chemical Property:

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Technology Process of ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside

There total 11 articles about ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-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: 95.0%

benzaldehyde (100-52-7) + ethyl 4-bromo-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside (347382-90-5) → ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside (347382-91-6)

Guidance literature:

indium; In water; at 20 ℃; for 2h;

DOI:10.1021/jo001217e

Reference yield: 57.0%

benzaldehyde (100-52-7) + ethyl 4-bromo-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside (468076-81-5) → ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside (347382-91-6) + ethyl 4-C-[(S)-1-phenyl-1-hydroxymethyl]-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (468076-74-6)

Guidance literature:

With indium; In ethanol; water; at 20 ℃; for 5h;

DOI:10.1002/1615-4169(200206)344:3/4<319::AID-ADSC319>3.0.CO;2-S

Reference yield: 30.0%

benzaldehyde (100-52-7) + ethyl 2-bromo-2,3,4-trideoxy-β-D-erythro-hex-3-enopyranoside (468076-58-6) → 6-Hydroxy-trans,trans-2,4-hexadienal + ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside (347382-91-6) + ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-hex-3-enopyranoside (468076-65-5)

Guidance literature:

With indium; In ethanol; water; at 20 ℃; for 7h;

DOI:10.1002/1615-4169(200206)344:3/4<319::AID-ADSC319>3.0.CO;2-S

upstream raw materials:

benzaldehyde

ethyl 4-bromo-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside

ethyl 4-bromo-2,3,4-trideoxy-α-D-erythro-hex-2-enopyranoside

ethyl 2-bromo-2,3,4-trideoxy-β-D-erythro-hex-3-enopyranoside

Downstream raw materials:

(S)-Phenyl-(1R,5S,6R)-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]non-5-yl-methanol

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