Toluene-4-sulfonic acid (2S,3S)-3-{(R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2S,3S)-3-{(R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranylmethyl ester
CAS No.:183308-67-0
Molecular Formula:C₂₈H₄₆O₈SSi
Molecular Weight:570.82
Hs Code.:

Toluene-4-sulfonic acid (2S,3S)-3-{(R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (2S,3S)-3-{(R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2S,3S)-3-{(R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranylmethyl ester

There total 10 articles about Toluene-4-sulfonic acid (2S,3S)-3-{(R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranylmethyl 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: 96.0%

: 98-59-9
p-toluenesulfonyl chloride

: 183308-75-0
((2S,3S)-3-{(R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranyl)-methanol

: 183308-67-0
Toluene-4-sulfonic acid (2S,3S)-3-{(R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranylmethyl ester

Guidance literature:: With triethylamine;
DOI:10.1016/0040-4039(96)01589-4

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 183308-67-0
Toluene-4-sulfonic acid (2S,3S)-3-{(R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / pyridine / CH₂Cl₂

2: 82 percent / t-BuLi / tetrahydrofuran / -78 deg C -> RT

3: 85 percent / Red-Al / diethyl ether / Ambient temperature

4: 92 percent / L-(+)-diethyl tartrate / CH₂Cl₂ / -25 °C

5: 96 percent / NEt₃

With pyridine; diethyl (2R,3R)-tartrate; tert.-butyl lithium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/0040-4039(96)01589-4

Reference yield:

: 183308-65-8
(S)-2,2-Dimethyl-4-((2R,5R)-(R)-5-oxiranyl-tetrahydro-furan-2-yl)-[1,3]dioxolane

: 183308-67-0
Toluene-4-sulfonic acid (2S,3S)-3-{(R)-3-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / diethyl ether / 0 °C

2: 98 percent / pyridine / CH₂Cl₂

3: 82 percent / t-BuLi / tetrahydrofuran / -78 deg C -> RT

4: 85 percent / Red-Al / diethyl ether / Ambient temperature

5: 92 percent / L-(+)-diethyl tartrate / CH₂Cl₂ / -25 °C

6: 96 percent / NEt₃

With pyridine; diethyl (2R,3R)-tartrate; tert.-butyl lithium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/0040-4039(96)01589-4