(1S,1S,2S,3S,4'R,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

Base Information

• Chemical Name: (1S,1S,2S,3S,4'R,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
• CAS No.: 202199-20-0
• Molecular Formula: C₄₈H₈₈N₂O₆Si₂
• Molecular Weight: 845.408
• Mol file: 202199-20-0.mol

Synonyms:(1S,1S,2S,3S,4'R,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

Chemical Property of (1S,1S,2S,3S,4'R,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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,1S,2S,3S,4'R,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

There total 24 articles about (1S,1S,2S,3S,4'R,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 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:

(3R)-3-(methoxymethoxy)-1-nonanol (181211-26-7) → (1S,1S,2S,3S,4'R,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 (202199-20-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 92 percent / CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 83 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 4.5 h / -78 - 0 °C

3.1: 96 percent / H₂ / Pd/C / ethanol / 20 h / 760 Torr

4.1: 88 percent / CBr₄; Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 86 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / 10.5 h / -78 - 0 °C

6.1: 96 percent / HCl / methanol / 0.5 h / 60 °C

7.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

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

8.2: 93 percent / imidazole / tetrahydrofuran / 10 h / 0 - 20 °C

9.1: 85 percent / formic acid / diethyl ether / 0.5 h / 0 °C

10.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

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

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 1.1: Bromination / 2.1: Addition / 3.1: Reduction / 4.1: Bromination / 5.1: Addition / 6.1: Elimination / 7.1: Etherification / 8.1: Reduction / 8.2: Etherification / 9.1: Elimination / 10.1: Swern oxidation / 11.1: Addition;

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

Reference yield:

1-bromo-(3R)-3-(methoxymethoxy)nonane (181211-28-9) → (1S,1S,2S,3S,4'R,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 (202199-20-0)

Guidance literature:

Multi-step reaction with 10 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

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 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;

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

Reference yield:

S-ethyl (R)-3-hydroxynonanethioate (181211-25-6) → (1S,1S,2S,3S,4'R,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 (202199-20-0)

Guidance literature:

Multi-step reaction with 13 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

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; carbon tetrabromide; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 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;

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

upstream raw materials:

(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine

(2R,3S,12R)-2-benzyloxy-3,12-di(tert-butyldimethylsiloxy)-octadec-4-enal

heptanal

(4S,5S)-5-benzyloxy-4-ethynyl-2,2-dimethyl-1,3-dioxane

Downstream raw materials:

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