(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]-2-(toluene-p-sulfonyloxy)ethanol

Base Information

Chemical Name:(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]-2-(toluene-p-sulfonyloxy)ethanol
CAS No.:155300-03-1
Molecular Formula:C₂₄H₃₂O₆S
Molecular Weight:448.58
Hs Code.:

Synonyms:(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]-2-(toluene-p-sulfonyloxy)ethanol

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Chemical Property of (1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]-2-(toluene-p-sulfonyloxy)ethanol

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Technology Process of (1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]-2-(toluene-p-sulfonyloxy)ethanol

There total 1 articles about (1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]-2-(toluene-p-sulfonyloxy)ethanol 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:

: 98-59-9
p-toluenesulfonyl chloride

: 155300-02-0
(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethane-1,2-diol

: 155300-03-1
(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]-2-(toluene-p-sulfonyloxy)ethanol

Guidance literature:: With di(n-butyl)tin oxide; triethylamine; Yield given. Multistep reaction; 1.) MeOH, heating;
DOI:10.1016/S0040-4039(00)76542-7

Reference yield: 92.0%

: 155300-03-1
(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]-2-(toluene-p-sulfonyloxy)ethanol

: 155300-04-2
(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]ethanol

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)76542-7

Reference yield:

: 155300-03-1
(1S,1''S,2'R,4'S,5'R)-(-)-1-[Tetrahydro-5'-(2''-benzyloxy-1''-methylethyl)-4'-methylfuran-2'-yl]-2-(toluene-p-sulfonyloxy)ethanol

: 155846-43-8
(3E,1''S,2S,2'R,3'S,5'R,8R)-9-Benzyloxy-8-methyl-2-[tetrahydro-5'-(1''-methoxyethyl)-3'-methylfuran-2'-yl]non-3-en-5-one

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / LiEt₃BH / tetrahydrofuran / 6 h / Ambient temperature

2: 90 percent / KH / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 3 h

3: 95 percent / H₂ / 10percent Pd/C / methanol / 16 h

4: 93 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂

5: 1.) LiCl, 2.) diisopropylethylamine / 1.) MeCN, 10 min, 2.) MeCN, 16 h

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; potassium hydride; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/a804170i