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

Base Information

Chemical Name:(1R,2R,2'R,5R,5R')-1-[5-(5'-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2'-yl)tetrahydrofuran-2-yl]-15-benzyloxypentadecan-1-ol
CAS No.:286853-91-6
Molecular Formula:C₃₇H₆₆O₅Si
Molecular Weight:619.014
Hs Code.:

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

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

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

There total 17 articles about (1R,2R,2'R,5R,5R')-1-[5-(5'-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2'-yl)tetrahydrofuran-2-yl]-15-benzyloxypentadecan-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: 96.0%

: 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

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

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -95 ℃;
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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 286853-81-4
(2R,2R',5R, 5R')-[5-(5'-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2'-yl)tetrahydrofuran-2-yl]methanol

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 - 0 °C

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

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

3.1: 72 percent / PCC / CH₂Cl₂ / 1 h / 20 °C

4.1: 96 percent / L-selectride / tetrahydrofuran / 2 h / -78 - -70 °C

With oxalyl dichloride; L-Selectride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Grignard reaction / 3.1: Oxidation / 4.1: Reduction;
DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R