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

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,4S,6R,8S,10S)-4-(tert-butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-10-hydroxy-4-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester
• CAS No.: 201868-10-2
• Molecular Formula: C₄₂H₆₂O₈SSi₂
• Molecular Weight: 783.186

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about Toluene-4-sulfonic acid (2R,4S,6R,8S,10S)-4-(tert-butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-10-hydroxy-4-methyl-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: 78.0%

Toluene-4-sulfonic acid (2R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-5-{2-[(2S,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dihydroxy-hexyl]-[1,3]dithian-2-yl}-2-hydroxy-4-methyl-pentyl ester (201868-01-1) → Toluene-4-sulfonic acid (2R,4S,6R,8S,10S)-4-(tert-butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-10-hydroxy-4-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (201868-10-2) + Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-4-(tert-butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-10-hydroxy-4-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (201868-09-9)

Guidance literature:

With mercury(II) perchlorate tetrahydrate; water; calcium carbonate; In acetonitrile; at 20 ℃; for 1h; optical yield given as %de;

DOI:10.1016/j.tet.2009.04.001

Reference yield: 77.0%

Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-4-(tert-butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-10-hydroxy-4-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (201868-09-9) → Toluene-4-sulfonic acid (2R,4S,6R,8S,10S)-4-(tert-butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-10-hydroxy-4-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (201868-10-2)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(97)10501-9

Reference yield:

ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methyl-2-propenoate (127642-52-8) → Toluene-4-sulfonic acid (2R,4S,6R,8S,10S)-4-(tert-butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-10-hydroxy-4-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (201868-10-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / DIBAL / CH₂Cl₂

2: TBHP, (-)-DET, Ti(O-i-Pr)4 / CH₂Cl₂ / -20 °C

3: 93 percent / LiBH₄, Ti(O-i-Pr)4 / toluene / 0 °C

4: 93 percent / tosylimidazole, NaH / tetrahydrofuran / 0 °C

5: t-BuLi / diethyl ether / -78 deg C -> -45 deg C, 1 h; -78 deg C -> -25 deg C, 1 h

6: 65 percent / HMPA / diethyl ether / -78 deg C -> RT

7: 90 percent / TFA / CH₂Cl₂; H₂O / 0 °C

8: 88 percent / DMAP / CH₂Cl₂

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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium borohydride; mercury(II) perchlorate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; (-)-diethyl tartrate; N-tosylimidazole; trifluoroacetic acid; calcium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/S0040-4039(97)10501-9

upstream raw materials:

Toluene-4-sulfonic acid (2R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-5-{2-[(2S,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dihydroxy-hexyl]-[1,3]dithian-2-yl}-2-hydroxy-4-methyl-pentyl ester

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

tert-butyl(1,3-dithian-2-yl)dimethylsilane

ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methyl-2-propenoate

Downstream raw materials:

(2R,4S,6R,8S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-iodomethyl-4-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undecane

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