(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran

Base Information

Chemical Name:(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran
CAS No.:400746-71-6
Molecular Formula:C₅₉H₈₃NO₉Si₂
Molecular Weight:1006.48
Hs Code.:

(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran

Synonyms:(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran

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Chemical Property of (2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran

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Technology Process of (2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran

There total 8 articles about (2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran 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: 94.0%

: 211691-10-0
7,7-ethylenedioxy-1-tridecene

: 400746-60-3
(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[3'-iodo-1'-[2-(trimethylsilyl)ethoxymethoxy]prop-2'-en-1'-yl]-2-oxo-tetrahydrofuran

: 400746-71-6
(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran

Guidance literature:: 7,7-ethylenedioxy-1-tridecene; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; for 2h;

(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[3'-iodo-1'-[2-(trimethylsilyl)ethoxymethoxy]prop-2'-en-1'-yl]-2-oxo-tetrahydrofuran; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;
DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

: 344615-51-6
(1'S,3S,4R,5S)-3-azido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran

: 400746-71-6
(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

2.1: 0.21 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

3.1: 82 percent / H₂SO₄ / H₂O; acetone / 3 h / 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 48 mg / CrCl₂ / tetrahydrofuran / 3 h / 0 - 20 °C

6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 20 °C

6.2: 94 percent / Ph₃As; Cs₂CO₃; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium / tetrahydrofuran; H₂O; dimethylformamide / 2 h / 0 - 20 °C

With chromium dichloride; dmap; sulfuric acid; hydrogen; Dess-Martin periodane; triethylamine; 9-bora-bicyclo[3.3.1]nonane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; 6.2: Suzuki-Miyaura reaction;
DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

: 344615-50-5
(2S,3R,4R,5S)-N,N-dimethyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide

: 400746-71-6
(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 3 h / 20 °C

1.2: 62 percent / pyridinium p-toluenesulfonate / toluene / 24 h / 70 °C

2.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3.1: 0.21 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

4.1: 82 percent / H₂SO₄ / H₂O; acetone / 3 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 48 mg / CrCl₂ / tetrahydrofuran / 3 h / 0 - 20 °C

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 20 °C

7.2: 94 percent / Ph₃As; Cs₂CO₃; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium / tetrahydrofuran; H₂O; dimethylformamide / 2 h / 0 - 20 °C

With chromium dichloride; dmap; sulfuric acid; hydrogen; Dess-Martin periodane; triethylamine; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; 7.2: Suzuki-Miyaura reaction;
DOI:10.1016/S0040-4020(02)01058-X