Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester
CAS No.:201275-54-9
Molecular Formula:C₃₁H₅₆O₈SSi₂
Molecular Weight:645.018
Hs Code.:

Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Synonyms:Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

There total 17 articles about Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl 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: 87.0%

: 98-59-9
p-toluenesulfonyl chloride

: [(2S,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-methanol

: 201275-54-9
Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;
DOI:10.1016/j.tet.2009.04.001

Reference yield:

: (2S,4S)-5-[2-((2S,4R)-5-Benzyloxy-2,4-dihydroxy-pentyl)-[1,3]dithian-2-yl]-4-methoxy-pentane-1,2-diol

: 201275-54-9
Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Hg(ClO₄)2, CaCO₃ / acetonitrile; H₂O

2: HClO₄ / CH₂Cl₂; acetonitrile

3: 70 percent / Et₃N

4: 89 percent / imidazole / dimethylformamide

5: H₂, CaCO₃ / Pd/C

6: imidazole

7: DIBAL / tetrahydrofuran / -50 °C

8: Et₃N / 0 °C

With 1H-imidazole; perchloric acid; mercury(II) perchlorate; hydrogen; diisobutylaluminium hydride; triethylamine; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(97)10500-7

Reference yield:

: 127793-60-6
(2R)-1-[(4S)-2,2-diethyl-[1,3]dioxolan-4-yl]-pent-4-en-2-ol

: 201275-54-9
Toluene-4-sulfonic acid (2S,4S,6S,8R,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-triethylsilanyloxymethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 98 percent / NaH, 15-cr-5

2: 96 percent / O₃, Ph₃P / CH₂Cl₂ / -78 °C

3: 89 percent / BF₃*Et₂O

4: 90 percent / PPTs

5: 20 percent / t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

6: 95 percent / i-Pr₂NEt / CH₂Cl₂

7: 85 percent / HCl / methanol

8: Hg(ClO₄)2, CaCO₃ / acetonitrile; H₂O

9: HClO₄ / CH₂Cl₂; acetonitrile

10: 70 percent / Et₃N

11: 89 percent / imidazole / dimethylformamide

12: H₂, CaCO₃ / Pd/C

13: imidazole

14: DIBAL / tetrahydrofuran / -50 °C

15: Et₃N / 0 °C

With 1H-imidazole; hydrogenchloride; perchloric acid; mercury(II) perchlorate; 15-crown-5; boron trifluoride diethyl etherate; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(97)10500-7