Toluene-4-sulfonic acid (3R,4R,5S)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (3R,4R,5S)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester
CAS No.:201278-63-9
Molecular Formula:C₂₅H₄₆O₆SSi₂
Molecular Weight:530.874
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (3R,4R,5S)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

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Chemical Property of Toluene-4-sulfonic acid (3R,4R,5S)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

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Technology Process of Toluene-4-sulfonic acid (3R,4R,5S)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

There total 14 articles about Toluene-4-sulfonic acid (3R,4R,5S)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester 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: 66.0%

: 98-59-9
p-toluenesulfonyl chloride

: 201278-58-2
(3R,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-ol

: 201278-63-9
Toluene-4-sulfonic acid (3R,4R,5S)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Guidance literature:: With pyridine; at 0 - 21 ℃; for 18h;
DOI:10.1021/jo971890c

Reference yield:

: 201278-35-5
(2R,3S)-4-(4-Bromo-benzyloxy)-2-vinyl-butane-1,3-diol

: 201278-63-9
Toluene-4-sulfonic acid (3R,4R,5S)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 79 percent / triethylamine, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 16 h / 21 °C

2: 90 percent / pyridine / CH₂Cl₂ / 18 h / 0 - 21 °C

3: 52 percent / silver(I) bis(sym-collidine) perchlorate, iodine / CH₂Cl₂ / 18 h / 21 °C

4: 56 percent / dimethylsulfoxide / 80 °C

5: 98 percent / ammonia / methanol / 18 h / 0 - 21 °C

6: 77 percent / triethylamine, (N,N-dimethylmino)pyridine / CH₂Cl₂ / 18 h

7: 66 percent / pyridine / 18 h / 0 - 21 °C

With pyridine; dmap; bis(2,4,6-trimethylpyridine)silver(I) perchlorate; (N,N-dimethylmino)pyridine; ammonia; iodine; triethylamine; In methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo971890c

Reference yield:

: 201279-13-2
(3R,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-tetrahydro-furan-3-ol

: 201278-63-9
Toluene-4-sulfonic acid (3R,4R,5S)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N, DMAP / CH₂Cl₂

2: pyridine / 18 h / 0 - 20 °C

With dmap; triethylamine; In pyridine; dichloromethane; 1: Substitution / 2: Tosylation;
DOI:10.1080/15257779908041490