(3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

Base Information

• Chemical Name: (3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene
• CAS No.: 116724-52-8
• Molecular Formula: C₃₁H₆₁O₈PSi₂
• Molecular Weight: 648.965
• Mol file: 116724-52-8.mol

Synonyms:(3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

Chemical Property of (3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

There total 13 articles about (3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene 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:

tert-butyldimethylsilyl chloride (18162-48-6) → (3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene (116724-52-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 9 h / Ambient temperature

2: 35.4 g / diisobutylaluminum hydride / hexane; tetrahydrofuran / 1.) -78 deg C, 2 h; 2.) 30 min, 0 deg C

3: 86 percent / triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / Ambient temperature

4: 74 percent / bromine / CH₂Cl₂ / 0.17 h / -78 °C

5: 92 percent / DBU / benzene / 7.5 h / Heating

6: tert-butyllithium / pentane; diethyl ether / 0.33 h / -78 °C

7: 1.) 2-thienylcyanocopperlithium / 1.) THF, pentane, ether, -78 deg C, 1 h; 2.) 3 h, -78 deg C

8: 1.) NaH / 1.) room t., 20 min, THF; 2.) 0 deg C, 2 h

With bromine; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; dmap; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane; benzene;

DOI:10.1021/ja00232a027

Reference yield:

2-(tert-butyl-dimethyl-silanyloxymethyl)-prop-2-en-1-ol (116700-73-3) → (3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene (116724-52-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / Ambient temperature

2: 74 percent / bromine / CH₂Cl₂ / 0.17 h / -78 °C

3: 92 percent / DBU / benzene / 7.5 h / Heating

4: tert-butyllithium / pentane; diethyl ether / 0.33 h / -78 °C

5: 1.) 2-thienylcyanocopperlithium / 1.) THF, pentane, ether, -78 deg C, 1 h; 2.) 3 h, -78 deg C

6: 1.) NaH / 1.) room t., 20 min, THF; 2.) 0 deg C, 2 h

With bromine; tert.-butyl lithium; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; dmap; In diethyl ether; dichloromethane; pentane; benzene;

DOI:10.1021/ja00232a027

Reference yield:

ethyl 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)acrylate (116700-77-7) → (3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene (116724-52-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 35.4 g / diisobutylaluminum hydride / hexane; tetrahydrofuran / 1.) -78 deg C, 2 h; 2.) 30 min, 0 deg C

2: 86 percent / triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / Ambient temperature

3: 74 percent / bromine / CH₂Cl₂ / 0.17 h / -78 °C

4: 92 percent / DBU / benzene / 7.5 h / Heating

5: tert-butyllithium / pentane; diethyl ether / 0.33 h / -78 °C

6: 1.) 2-thienylcyanocopperlithium / 1.) THF, pentane, ether, -78 deg C, 1 h; 2.) 3 h, -78 deg C

7: 1.) NaH / 1.) room t., 20 min, THF; 2.) 0 deg C, 2 h

With bromine; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; dmap; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane; benzene;

DOI:10.1021/ja00232a027

upstream raw materials:

diethyl chlorophosphate

(1S,2S,3R)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-3-isopropyl-6-oxo-cyclohexanecarboxylic acid methyl ester

4-isopropyl-cyclohexanone

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

(2SR,3RS,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-methylene-3-<3-acetoxy-2-(acetoxymethyl)propen-1-yl>cyclohexane