(Z)-7-{(1R,6S)-2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,6-dihydroxy-cyclohexyl}-hept-5-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-7-{(1R,6S)-2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,6-dihydroxy-cyclohexyl}-hept-5-enoic acid methyl ester
• CAS No.: 74271-59-3
• Molecular Formula: C₂₈H₅₂O₅Si
• Molecular Weight: 496.803
• Mol file: 74271-59-3.mol

Synonyms:

Chemical Property of (Z)-7-{(1R,6S)-2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,6-dihydroxy-cyclohexyl}-hept-5-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-{(1R,6S)-2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,6-dihydroxy-cyclohexyl}-hept-5-enoic acid methyl ester

There total 6 articles about (Z)-7-{(1R,6S)-2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,6-dihydroxy-cyclohexyl}-hept-5-enoic acid methyl ester 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:

PGA2 methyl ester 15-t-butyldimethylsilyl ether (53122-04-6) → (Z)-7-{(1R,6S)-2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,6-dihydroxy-cyclohexyl}-hept-5-enoic acid methyl ester (74271-59-3,74310-82-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 50 percent / potassium cyanide/18-crown-6, neopentyl alcohol / CHCl₃

2: lithium aluminium hydride

3: 28 percent / nitrous acid / 0.17 h / 25 °C

5: alkaline hydrogen peroxide

6: 1.) aluminum amalgam; 2.) L-Selectide reduction / 2.) -78 deg C

With potassium cyanide; lithium aluminium tetrahydride; 18-crown-6 ether; 2,2-dimethyl-propanol-1; aluminium amalgam; alkaline hydrogen peroxide; cis-nitrous acid; In chloroform;

DOI:10.1016/S0040-4039(00)71428-6

Reference yield:

(Z)-7-{(R)-4-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-2-oxo-7-oxa-bicyclo[4.1.0]hept-3-yl}-hept-5-enoic acid methyl ester → (Z)-7-{(1R,6S)-2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,6-dihydroxy-cyclohexyl}-hept-5-enoic acid methyl ester (74271-59-3,74310-82-0)

Guidance literature:

With aluminium amalgam; Multistep reaction; 2.) -78 deg C;

DOI:10.1016/S0040-4039(00)71428-6

Reference yield:

(R)-1-Aminomethyl-4-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-((Z)-7-hydroxy-hept-2-enyl)-cyclopent-2-enol (74271-54-8) → (Z)-7-{(1R,6S)-2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,6-dihydroxy-cyclohexyl}-hept-5-enoic acid methyl ester (74271-59-3,74310-82-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 28 percent / nitrous acid / 0.17 h / 25 °C

3: alkaline hydrogen peroxide

4: 1.) aluminum amalgam; 2.) L-Selectide reduction / 2.) -78 deg C

With aluminium amalgam; alkaline hydrogen peroxide; cis-nitrous acid;

DOI:10.1016/S0040-4039(00)71428-6

upstream raw materials:

PGA₂ methyl ester 15-t-butyldimethylsilyl ether

(R)-1-Aminomethyl-4-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-((Z)-7-hydroxy-hept-2-enyl)-cyclopent-2-enol

(R)-5-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-6-((Z)-7-hydroxy-hept-2-enyl)-cyclohex-3-enone

(Z)-7-{(R)-6-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-2-oxo-cyclohex-3-enyl}-hept-5-enoic acid methyl ester