ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-hex-3-enopyranoside

Base Information

Chemical Name:ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-hex-3-enopyranoside
CAS No.:468076-65-5
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-hex-3-enopyranoside

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Chemical Property of ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-hex-3-enopyranoside

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Technology Process of ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-hex-3-enopyranoside

There total 6 articles about ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-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: 30.0%

: 100-52-7
benzaldehyde

: 468076-58-6
ethyl 2-bromo-2,3,4-trideoxy-β-D-erythro-hex-3-enopyranoside

: 6-Hydroxy-trans,trans-2,4-hexadienal

: 347382-91-6
ethyl 2-C-[(S)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-α-D-threo-hex-3-enopyranoside

: 468076-65-5
ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-hex-3-enopyranoside

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

Reference yield: 22.0%

: 100-52-7
benzaldehyde

: 468076-83-7
ethyl 4-bromo-2,3,4-trideoxy-β-D-erythro-hex-2-enopyranoside

: 468076-65-5
ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-hex-3-enopyranoside

Guidance literature:: With indium; In ethanol; water; at 20 ℃; for 1h;
DOI:10.1002/1615-4169(200206)344:3/4<319::AID-ADSC319>3.0.CO;2-S

Reference yield:

: 187990-51-8
ethyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside

: 468076-65-5
ethyl 2-C-[(R)-1-phenyl-1-hydroxymethyl]-3,4-dideoxy-β-D-erythro-hex-3-enopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: benzoic acid; Ph₃P; diisopropyl azidodicarboxylate / tetrahydrofuran / 3 h / 20 °C

1.2: 54 percent / sodium methoxide / methanol / 20 °C

2.1: Ph₃P; CBr₄ / CH₂Cl₂ / 0 °C

3.1: NBu₄⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 3 h / 20 °C

4.1: 22 percent / indium powder / ethanol; H₂O / 1 h / 20 °C

With indium; carbon tetrabromide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; benzoic acid; In tetrahydrofuran; ethanol; dichloromethane; water; 1.1: Mitsunobu reaction / 4.1: Barbier allylation;
DOI:10.1002/1615-4169(200206)344:3/4<319::AID-ADSC319>3.0.CO;2-S