(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

Base Information

Chemical Name:(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
CAS No.:286853-93-8
Molecular Formula:C₃₇H₆₄O₅Si
Molecular Weight:616.998
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 1 articles about (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 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: 90.0%

: 286853-92-7
(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]methanol

: 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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - 0 ℃;
DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R

Reference yield:

: 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

: 120298-30-8
squamocin

Guidance literature:: Multi-step reaction with 10 steps

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

1.2: diethyl ether

2.1: 2,6-lutidine / CH₂Cl₂ / 2 h / -20 °C

3.1: 10percent Pd/C / propan-2-ol / 20 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -50 - 0 °C

5.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

6.1: LDA; LiCl / tetrahydrofuran / 0.5 h / 20 °C

6.2: tetrahydrofuran / 20 °C

7.1: pivaloyl chloride; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

8.1: LDA / tetrahydrofuran / 0 °C

8.2: tetrahydrofuran / 2 h / 0 - 20 °C

9.1: monoperoxyphthalic acid / tetrahydrofuran; methanol / 0.5 h / 20 °C

10.1: 82 percent / HF (5percent in CH₃CN) / tetrahydrofuran / 6 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; monoperoxyphthalic acid; 2-methyl-but-2-ene; oxalyl dichloride; pivaloyl chloride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; lithium chloride; lithium diisopropyl amide; 10percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; tert-butyl alcohol; 1.1: Metallation / 1.2: Grignard reaction / 2.1: silylation / 3.1: Hydrogenolysis / 4.1: Oxidation / 5.1: Oxidation / 6.1: Metallation / 6.2: Substitution / 7.1: Cyclization / 8.1: Metallation / 8.2: Substitution / 9.1: Oxidation / 10.1: desilylation;
DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R

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