(E)-(4R,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid tert-butyl ester

Base Information

Chemical Name:(E)-(4R,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid tert-butyl ester
CAS No.:221103-29-3
Molecular Formula:C₃₂H₃₈O₆
Molecular Weight:518.65
Hs Code.:

Synonyms:(E)-(4R,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid tert-butyl ester

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Chemical Property of (E)-(4R,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid tert-butyl ester

Chemical Property:

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Technology Process of (E)-(4R,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid tert-butyl ester

There total 1 articles about (E)-(4R,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid tert-butyl ester 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: 92.0%

: 160549-10-0
2,3,5-tri-O-benzyl-D-arabinofuranose

: 86302-43-4,35000-38-5
(tert-Butoxycarbonylmethylene)triphenylphosphorane

: 221103-29-3
(E)-(4R,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid tert-butyl ester

Guidance literature:: In dichloromethane; at 25 ℃;
DOI:10.1021/ja00271a049

Reference yield:

: 221103-29-3
(E)-(4R,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid tert-butyl ester

: 101932-68-7
(1R,2R,3S,4S)-2,3-bis(benzyloxy)-4-<(benzyloxy)methyl>-4-hydroxycyclopentanylmethanol

Guidance literature:: Multi-step reaction with 8 steps

1: DMSO/(COCl)2, EtN₃

2: 93 percent / CF₃COOH / CH₂Cl₂ / 0 °C

3: 1.) LDA; 2.) LDA / 2.) -78 deg C

4: Bu₃SnH / benzene / 25 °C

6: AcOH

7: O₃

8: NaBH₄

With sodium tetrahydroborate; oxalyl dichloride; tri-n-butyl-tin hydride; ozone; acetic acid; dimethyl sulfoxide; trifluoroacetic acid; lithium diisopropyl amide; ethyl azide; In dichloromethane; benzene;
DOI:10.1021/ja00271a049

Reference yield:

: 221103-29-3
(E)-(4R,5R,6R)-4,5,7-Tris-benzyloxy-6-hydroxy-hept-2-enoic acid tert-butyl ester

: (1S,5R,6R,7S)-6,7-Bis-benzyloxy-1-benzyloxymethyl-2-oxa-bicyclo[3.2.1]octan-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: DMSO/(COCl)2, EtN₃

2: 93 percent / CF₃COOH / CH₂Cl₂ / 0 °C

3: 1.) LDA; 2.) LDA / 2.) -78 deg C

4: Bu₃SnH / benzene / 25 °C

5: 60 percent / DBU / benzene / 80 °C

With oxalyl dichloride; tri-n-butyl-tin hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium diisopropyl amide; ethyl azide; In dichloromethane; benzene;
DOI:10.1021/ja00271a049