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

Base Information

Chemical Name:(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1,5-di(tert-butyldimethylsilyloxy)undecane
CAS No.:337954-15-1
Molecular Formula:C₃₉H₇₂O₅Si₂
Molecular Weight:677.169
Hs Code.:

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

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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]-1,5-di(tert-butyldimethylsilyloxy)undecane

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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]-1,5-di(tert-butyldimethylsilyloxy)undecane

There total 8 articles about (1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1,5-di(tert-butyldimethylsilyloxy)undecane 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: 99.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

: 337954-15-1
(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1,5-di(tert-butyldimethylsilyloxy)undecane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -20 - 0 ℃; for 2h;
DOI:10.1002/1521-3765(20010302)7:5<993::AID-CHEM993>3.0.CO;2-S

Reference yield:

: 100-39-0
benzyl bromide

: 337954-15-1
(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1,5-di(tert-butyldimethylsilyloxy)undecane

Guidance literature:: Multi-step reaction with 6 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

6.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -20 - 0 °C

With 2,6-dimethylpyridine; 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:

: 250138-84-2
(all-R)-5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-carbaldehyde

: 337954-15-1
(1R,5S,2'R,5'R,2''R,5''R)-1-[5'-(5''-Benzyloxymethyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1,5-di(tert-butyldimethylsilyloxy)undecane

Guidance literature:: Multi-step reaction with 4 steps

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

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

1.3: 74 percent / diethyl ether / -60 - 20 °C

2.1: 60 percent / PCC; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

3.1: 77 percent / L-Selectride / tetrahydrofuran / 1.5 h / -110 - -60 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -20 - 0 °C

With 2,6-dimethylpyridine; 4 A molecular sieve; L-Selectride; magnesium; ethylene dibromide; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; 1.3: Grignard reaction;
DOI:10.1002/1521-3765(20010302)7:5<993::AID-CHEM993>3.0.CO;2-S