diethyl (3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-3,9-dihydroxy-2,2,6,6,10,10-hexamethylundecanedioate

Base Information

• Chemical Name: diethyl (3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-3,9-dihydroxy-2,2,6,6,10,10-hexamethylundecanedioate
• CAS No.: 268750-40-9
• Molecular Formula: C₃₅H₅₂O₈
• Molecular Weight: 600.793
• Mol file: 268750-40-9.mol

Synonyms:diethyl (3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-3,9-dihydroxy-2,2,6,6,10,10-hexamethylundecanedioate

Chemical Property of diethyl (3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-3,9-dihydroxy-2,2,6,6,10,10-hexamethylundecanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-3,9-dihydroxy-2,2,6,6,10,10-hexamethylundecanedioate

There total 11 articles about diethyl (3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-3,9-dihydroxy-2,2,6,6,10,10-hexamethylundecanedioate 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: 77.0%

1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene (31469-16-6) + (3RS,5SR)-3,5-dibenzyloxy-4,4-dimethylheptane-1,7-dial (268750-39-6) → diethyl (3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-3,9-dihydroxy-2,2,6,6,10,10-hexamethylundecanedioate (268750-40-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -90 ℃; for 20h;

DOI:10.1021/ol0056325

Reference yield:

5,5-dimethyl-1,8-nonadiene-4,6-diol (446264-32-0) → diethyl (3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-3,9-dihydroxy-2,2,6,6,10,10-hexamethylundecanedioate (268750-40-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 57 percent / NaH; Bu₄NI / dimethylformamide; tetrahydrofuran / 15 h / 20 °C

2: 92 percent / CF₃SO₃H / diethyl ether / 15 h

3: 88 percent / O₃ / CH₂Cl₂ / -78 °C

4: BF₃*Et₂O / CH₂Cl₂ / 20 h / -90 °C

With trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200204)2002:7<1292::AID-EJOC1292>3.0.CO;2-6

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → diethyl (3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-3,9-dihydroxy-2,2,6,6,10,10-hexamethylundecanedioate (268750-40-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / CF₃SO₃H / diethyl ether / 15 h

2: 88 percent / O₃ / CH₂Cl₂ / -78 °C

3: BF₃*Et₂O / CH₂Cl₂ / 20 h / -90 °C

With trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; ozone; In diethyl ether; dichloromethane;

DOI:10.1002/1099-0690(200204)2002:7<1292::AID-EJOC1292>3.0.CO;2-6

upstream raw materials:

1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene

(3RS,5SR)-3,5-dibenzyloxy-4,4-dimethylheptane-1,7-dial

O-benzyl 2,2,2-trichloroacetimidate

benzyl bromide

Downstream raw materials:

(3RS,5RS,7SR,9SR)-5,7-dibenzyloxy-2,2,6,6,10,10-hexamethylundecane-1,3,9,11-tetraol

Refernces

• 1、 Trieselmann, Thomas,Hoffmann, Reinhard W.. "Stereoselective synthesis of skipped polyols by substrate-directed asymmetric induction". . p. 1209 - 1212. Retrieved 2007/10/03.