ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate

Base Information

• Chemical Name: ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate
• CAS No.: 181210-26-4
• Molecular Formula: C₄₆H₈₅NO₈Si₂
• Molecular Weight: 836.354
• Mol file: 181210-26-4.mol

Synonyms:ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate

Chemical Property of ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate

There total 23 articles about ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate 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: 54.0%

di-tert-butyl dicarbonate (24424-99-5) + (1R,1R,2S,3S,4'S,12R)-2-benzyloxy-3,12-di(tert-butyldimethylsiloxy)-1-(3',6'-diethoxy-4'-(isopropyl)-1'H,4'H-2',5'-diazyl)-octadec-4-ene-1-ol (202199-22-2) → ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate (181210-26-4)

Guidance literature:

(1R,1R,2S,3S,4'S,12R)-2-benzyloxy-3,12-di(tert-butyldimethylsiloxy)-1-(3',6'-diethoxy-4'-(isopropyl)-1'H,4'H-2',5'-diazyl)-octadec-4-ene-1-ol; With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 0 ℃; for 3h;

di-tert-butyl dicarbonate; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/S0040-4020(98)00484-0

Reference yield:

1-bromo-(3R)-3-(methoxymethoxy)nonane (181211-28-9) → ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate (181210-26-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 83 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C

2.1: 96 percent / H₂ / Pd/C / ethanol / 20 h / 760 Torr

3.1: 88 percent / CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 86 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C

5.1: 96 percent / HCl / methanol / 0.5 h / 60 °C

6.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

7.1: LAH / tetrahydrofuran / 1 h / 0 - 20 °C

7.2: 93 percent / imidazole / tetrahydrofuran / 10 h / 0 - 20 °C

8.1: 85 percent / formic acid / diethyl ether / 0.5 h / 0 °C

9.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

10.1: n-BuLi; ZnCl₂ / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

11.1: TsOH / tetrahydrofuran; H₂O / 3 h / 0 °C

11.2: 54 percent / CH₂Cl₂ / 6 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; 1.1: Addition / 2.1: Reduction / 3.1: Bromination / 4.1: Addition / 5.1: Elimination / 6.1: Etherification / 7.1: Reduction / 7.2: Etherification / 8.1: Elimination / 9.1: Swern oxidation / 10.1: Addition / 11.1: Esterification / 11.2: Carboxylation;

DOI:10.1016/S0040-4020(98)00484-0

Reference yield:

S-ethyl (R)-3-hydroxynonanethioate (181211-25-6) → ethyl (2S,3R,4S,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-5,14-di(tert-butyldimethylsiloxy)-3-hydroxyeicos-6-enoate (181210-26-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 100 percent / diisopropylethylamine / CH₂Cl₂ / 10 h / 0 - 20 °C

2.1: 98 percent / LAH / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: 92 percent / CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 83 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C

5.1: 96 percent / H₂ / Pd/C / ethanol / 20 h / 760 Torr

6.1: 88 percent / CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 86 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C

8.1: 96 percent / HCl / methanol / 0.5 h / 60 °C

9.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

10.1: LAH / tetrahydrofuran / 1 h / 0 - 20 °C

10.2: 93 percent / imidazole / tetrahydrofuran / 10 h / 0 - 20 °C

11.1: 85 percent / formic acid / diethyl ether / 0.5 h / 0 °C

12.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

13.1: n-BuLi; ZnCl₂ / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

14.1: TsOH / tetrahydrofuran; H₂O / 3 h / 0 °C

14.2: 54 percent / CH₂Cl₂ / 6 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; 1.1: Etherification / 2.1: Reduction / 3.1: Bromination / 4.1: Addition / 5.1: Reduction / 6.1: Bromination / 7.1: Addition / 8.1: Elimination / 9.1: Etherification / 10.1: Reduction / 10.2: Etherification / 11.1: Elimination / 12.1: Swern oxidation / 13.1: Addition / 14.1: Esterification / 14.2: Carboxylation;

DOI:10.1016/S0040-4020(98)00484-0

upstream raw materials:

di-tert-butyl dicarbonate

(E)-(2S,3R,4S,5S,14R)-2-Amino-4-benzyloxy-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid ethyl ester

(1R,1R,2S,3S,4'S,12R)-2-benzyloxy-3,12-di(tert-butyldimethylsiloxy)-1-(3',6'-diethoxy-4'-(isopropyl)-1'H,4'H-2',5'-diazyl)-octadec-4-ene-1-ol

heptanal

Downstream raw materials:

(E)-(2S,3R,4S,5S,14R)-4-Benzyloxy-2-tert-butoxycarbonylamino-5,14-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-icos-6-enoic acid

(2S,3R,4R,5S,14R)-4-benzyloxy-2-(tert-butoxycarbonylamino)-3,5,14-trihydroxyeicos-6-enoic acid