Toluene-4-sulfonic acid (2R,3R)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-oxiranylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3R)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-oxiranylmethyl ester
CAS No.:341990-30-5
Molecular Formula:C₂₃H₃₈O₇SSi
Molecular Weight:486.702
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3R)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-oxiranylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3R)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-oxiranylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3R)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-oxiranylmethyl ester

There total 6 articles about Toluene-4-sulfonic acid (2R,3R)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-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: 98.0%

: 98-59-9
p-toluenesulfonyl chloride

: 341990-29-2
{(2R,3R)-3-[(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-oxiranyl}-methanol

: 341990-30-5
Toluene-4-sulfonic acid (2R,3R)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-oxiranylmethyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 3h;
DOI:10.1055/s-2001-11398

Reference yield:

: 22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7
2-deoxy-D-ribose

: 341990-30-5
Toluene-4-sulfonic acid (2R,3R)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-oxiranylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / tetrahydrofuran / 5 h / 80 °C

2: 93 percent / CSA / CH₂Cl₂ / 12 h / 40 °C

3: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 25 °C

4: 81 percent / DIBAL-H / diethyl ether / 5 h / 0 - 25 °C

5: 90 percent / Ti(OiPr)4; tBuOOH; (-)-diethyl tartrate / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 24 h / -20 °C

6: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; camphor-10-sulfonic acid; diisobutylaluminium hydride; (-)-diethyl tartrate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; decane; dichloromethane; 1: Wittig reaction / 5: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2001-11398

Reference yield:

: 78606-78-7
methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate

: 341990-30-5
Toluene-4-sulfonic acid (2R,3R)-3-[(4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-oxiranylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / CSA / CH₂Cl₂ / 12 h / 40 °C

2: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 25 °C

3: 81 percent / DIBAL-H / diethyl ether / 5 h / 0 - 25 °C

4: 90 percent / Ti(OiPr)4; tBuOOH; (-)-diethyl tartrate / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 24 h / -20 °C

5: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; camphor-10-sulfonic acid; diisobutylaluminium hydride; (-)-diethyl tartrate; triethylamine; 4 A molecular sieve; In diethyl ether; decane; dichloromethane; 4: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2001-11398