(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzoyloxy-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-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran
• CAS No.: 344615-57-2
• Molecular Formula: C₅₉H₈₁NO₁₀Si₂
• Molecular Weight: 1020.46
• Mol file: 344615-57-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (2'E,1'S,3S,4R,5R)-3-benzamido-4-benzoyloxy-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: 81.0%

2-[6-(9-Bora-bicyclo[3.3.1]non-9-yl)-hexyl]-2-hexyl-[1,3]dioxolane (344615-56-1) + (2'E,1'S,3S,4R,5R)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[3'-iodo-1'-[2-(trimethylsilyl)ethoxymethoxy]prop-2'-en-1'-yl]-2-oxo-tetrahydrofuran (344615-55-0) → (2'E,1'S,3S,4R,5R)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran (344615-57-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(01)00246-5

Reference yield:

(1'S,3S,4R,5S)-3-azido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran (344615-51-6) → (2'E,1'S,3S,4R,5R)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran (344615-57-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 61 percent / NaBrO₃; NaHSO₃ / ethyl acetate; H₂O / 1 h / 20 °C

2.1: H₂ / Pd/C / ethyl acetate / 14 h / 20 °C

3.1: 0.24 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 2 h / 20 °C

4.1: 87 percent / H₂SO₄ / H₂O; acetone / 13 h / 20 °C

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

6.1: 0.12 g / CrCl₂ / tetrahydrofuran / 3 h / 0 - 20 °C

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

7.2: 81 percent / Ph₃As; Cs₂CO₃; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium / tetrahydrofuran; H₂O; dimethylformamide / 2 h / 0 - 20 °C

With chromium dichloride; dmap; sodium bromate; sulfuric acid; hydrogen; Dess-Martin periodane; sodium hydrogensulfite; triethylamine; 9-bora-bicyclo[3.3.1]nonane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; 7.2: Suzuki-Miyaura reaction;

DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

(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 (344615-50-5) → (2'E,1'S,3S,4R,5R)-3-benzamido-4-benzoyloxy-3-(tert-butyldiphenylsilyloxymethyl)-5-[10',10'-ethylenedioxy-1'-[2-(trimethylsilyl)ethoxymethoxy]hexadec-2'-en-1'-yl]-2-oxo-tetrahydrofuran (344615-57-2)

Guidance literature:

Multi-step reaction with 8 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: 61 percent / NaBrO₃; NaHSO₃ / ethyl acetate; H₂O / 1 h / 20 °C

3.1: H₂ / Pd/C / ethyl acetate / 14 h / 20 °C

4.1: 0.24 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 2 h / 20 °C

5.1: 87 percent / H₂SO₄ / H₂O; acetone / 13 h / 20 °C

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

7.1: 0.12 g / CrCl₂ / tetrahydrofuran / 3 h / 0 - 20 °C

8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 20 °C

8.2: 81 percent / Ph₃As; Cs₂CO₃; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium / tetrahydrofuran; H₂O; dimethylformamide / 2 h / 0 - 20 °C

With chromium dichloride; dmap; sodium bromate; sulfuric acid; hydrogen; Dess-Martin periodane; sodium hydrogensulfite; 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; 8.2: Suzuki-Miyaura reaction;

DOI:10.1016/S0040-4020(02)01058-X

upstream raw materials:

2-[6-(9-Bora-bicyclo[3.3.1]non-9-yl)-hexyl]-2-hexyl-[1,3]dioxolane

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

benzoyl chloride

(1'S,3S,4R,5S)-3-azido-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-4-hydroxy-2-oxo-tetrahydrofuran

Downstream raw materials:

sphingofungin E

(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzoyloxy-3-hydroxymethyl-5-(1'-hydroxymethyl-10'-oxo-hexadec-2'-en-1'-yl)-2-oxo-tetrahydrofuran