(1R,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-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'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol
CAS No.:247586-73-8
Molecular Formula:C₅₃H₁₀₀O₆Si₂
Molecular Weight:889.544
Hs Code.:

(1R,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

Synonyms:(1R,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-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'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-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'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

There total 8 articles about (1R,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-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:

: 247586-72-7
(4S)-4-(tert-butyldimethylsilyloxy)-1-decyl bromide

: 286853-93-8
(1'''R,2'R,2''R,5'R,5''R)-[5-(5'-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]carbaldehyde

: 247586-73-8
(1R,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

: 247586-74-9
(1S,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

Guidance literature:: (4S)-4-(tert-butyldimethylsilyloxy)-1-decyl bromide; With magnesium; In diethyl ether;

(1'''R,2'R,2''R,5'R,5''R)-[5-(5'-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]carbaldehyde; With copper(I) bromide dimethylsulfide complex; In diethyl ether; at -78 - 25 ℃;
DOI:10.1016/S0040-4039(99)01225-3

Reference yield:

: 111-71-7
heptanal

: 247586-73-8
(1R,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: (R)-BINOL; mol sieves 4 Angstroem; Ti(OiPr)4 / CH₂Cl₂ / 1 h / 20 °C

1.2: 68 percent / CH₂Cl₂ / 120 h / -78 - -25 °C

2.1: 98 percent / imidazole / CH₂Cl₂; toluene / 20 °C

3.1: tetrahydrofuran / 18 h / 20 °C

4.1: NaOH; 30percent H₂O₂ / tetrahydrofuran / 5 h

5.1: 82 percent / pyridine / CH₂Cl₂ / 0 °C

6.1: 93 percent / LiBr / tetrahydrofuran / 32 h / 35 °C

7.1: Mg; BrCH₂CH₂Br / diethyl ether / 1 h / 35 °C

7.2: diethyl ether

With pyridine; 1H-imidazole; titanium(IV) isopropylate; sodium hydroxide; 4 A molecular sieve; (R)-1,1'-Bi-2-naphthol; magnesium; ethylene dibromide; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Addition / 1.2: Substitution / 2.1: silylation / 3.1: Addition / 4.1: Oxidation / 5.1: Tosylation / 6.1: Bromination / 7.1: Metallation / 7.2: Grignard reaction;
DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R

Reference yield:

: 123464-22-2
(S)-(-)-1-decen-4-ol

: 247586-73-8
(1R,5S,2'R,5'R,2''R,5''R,1'''R)-1-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-5-(tert-butyldimethylsilyloxy)undecan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / imidazole / CH₂Cl₂; toluene / 20 °C

2.1: tetrahydrofuran / 18 h / 20 °C

3.1: NaOH; 30percent H₂O₂ / tetrahydrofuran / 5 h

4.1: 82 percent / pyridine / CH₂Cl₂ / 0 °C

5.1: 93 percent / LiBr / tetrahydrofuran / 32 h / 35 °C

6.1: Mg; BrCH₂CH₂Br / diethyl ether / 1 h / 35 °C

6.2: diethyl ether

With pyridine; 1H-imidazole; sodium hydroxide; magnesium; ethylene dibromide; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: silylation / 2.1: Addition / 3.1: Oxidation / 4.1: Tosylation / 5.1: Bromination / 6.1: Metallation / 6.2: Grignard reaction;
DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R