(1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane

Base Information

Chemical Name:(1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane
CAS No.:286854-03-3
Molecular Formula:C₅₉H₁₁₄O₆Si₃
Molecular Weight:1003.81
Hs Code.:

(1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane

Synonyms:(1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane

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Chemical Property of (1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane

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Technology Process of (1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane

There total 10 articles about (1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane 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: 91.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

: 286854-03-3
(1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane

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

Reference yield:

: 111-71-7
heptanal

: 286854-03-3
(1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane

Guidance literature:: Multi-step reaction with 8 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

8.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 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 / 8.1: silylation;
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

: 286854-03-3
(1R,2'R,5'R,2''R,5''R,1'''R,5'''S)-1-[5'-(5''-(1''',5'''-bis(tert-butyldimethylsilyloxy)undec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecane

Guidance literature:: Multi-step reaction with 7 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

7.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 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 / 7.1: silylation;
DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R