(1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one

Base Information

Chemical Name:(1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one
CAS No.:286854-02-2
Molecular Formula:C₄₃H₈₀O₅Si₂
Molecular Weight:733.276
Hs Code.:

(1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one

Synonyms:(1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one

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Chemical Property of (1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one

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Technology Process of (1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one

There total 18 articles about (1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one 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: 87.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 286853-91-6
(1R,2R,2'R,5R,5R')-1-[5-(5'-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2'-yl)tetrahydrofuran-2-yl]-15-benzyloxypentadecan-1-ol

: 286854-02-2
(1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one

Guidance literature:: With 1H-imidazole;
DOI:10.1016/S0040-4039(99)01225-3

Reference yield:

: 286853-90-5
(2'R,2''R,5'R, 5R'')-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]carbaldehyde

: 286854-02-2
(1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: Mg; BrCH₂CH₂Br / diethyl ether / 1 h / Heating

1.2: diethyl ether / 3 h / -40 - 20 °C

2.1: 72 percent / PCC / CH₂Cl₂ / 1 h / 20 °C

3.1: 96 percent / L-selectride / tetrahydrofuran / 2 h / -78 - -70 °C

4.1: 87 percent / imidazole / CH₂Cl₂; toluene / 20 °C

With 1H-imidazole; L-Selectride; magnesium; ethylene dibromide; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Oxidation / 3.1: Reduction / 4.1: silylation;
DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R

Reference yield:

: 286854-01-1
(2R',2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-15-benzyloxypentadecan-1-one

: 286854-02-2
(1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / L-selectride / tetrahydrofuran / 2 h / -78 - -70 °C

2: 87 percent / imidazole / CH₂Cl₂; toluene / 20 °C

With 1H-imidazole; L-Selectride; In tetrahydrofuran; dichloromethane; toluene; 1: Reduction / 2: silylation;
DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R