(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

Base Information

Chemical Name:(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol
CAS No.:337954-06-0
Molecular Formula:C₃₃H₅₈O₅Si
Molecular Weight:562.906
Hs Code.:

Synonyms:(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

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Chemical Property of (1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

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Technology Process of (1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

There total 7 articles about (1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-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: 77.0%

: 337954-05-9
(5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-one

: 337954-06-0
(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -110 - -60 ℃; for 1.5h;
DOI:10.1002/1521-3765(20010302)7:5<993::AID-CHEM993>3.0.CO;2-S

Reference yield:

: 100-39-0
benzyl bromide

: 337954-06-0
(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 29 percent / NaH / tetrahydrofuran / 20 °C

2.1: 89 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 0.83 h / -45 - 0 °C

3.1: Mg; 1,2-dibromoethane / diethyl ether / 0.75 h / 20 - 35 °C

3.2: CuBr*Me₂S / diethyl ether / 0.25 h / -60 °C

3.3: 74 percent / diethyl ether / -60 - 20 °C

4.1: 60 percent / PCC; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

5.1: 77 percent / L-Selectride / tetrahydrofuran / 1.5 h / -110 - -60 °C

With oxalyl dichloride; 4 A molecular sieve; L-Selectride; sodium hydride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Swern oxidation / 3.3: Grignard reaction;
DOI:10.1002/1521-3765(20010302)7:5<993::AID-CHEM993>3.0.CO;2-S

Reference yield:

: 250138-83-1
(all-R)-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]methanol

: 337954-06-0
(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 0.83 h / -45 - 0 °C

2.1: Mg; 1,2-dibromoethane / diethyl ether / 0.75 h / 20 - 35 °C

2.2: CuBr*Me₂S / diethyl ether / 0.25 h / -60 °C

2.3: 74 percent / diethyl ether / -60 - 20 °C

3.1: 60 percent / PCC; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

4.1: 77 percent / L-Selectride / tetrahydrofuran / 1.5 h / -110 - -60 °C

With oxalyl dichloride; 4 A molecular sieve; L-Selectride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Swern oxidation / 2.3: Grignard reaction;
DOI:10.1002/1521-3765(20010302)7:5<993::AID-CHEM993>3.0.CO;2-S