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

Base Information

• Chemical Name: 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
• CAS No.: 201868-01-1
• Molecular Formula: C₄₅H₇₀O₈S₃Si₂
• Molecular Weight: 891.415

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 13 articles about 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 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%

p-toluenesulfonyl chloride (98-59-9) + (R)-2,2-Dimethyl-4-((S)-2-methyl-oxiranylmethyl)-[1,3]dioxolane (192047-55-5) + tert-Butyl-[2-((4S,6S)-6-[1,3]dithian-2-ylmethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-ethoxy]-diphenyl-silane → 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)

Guidance literature:

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

Reference yield: 88.0%

p-toluenesulfonyl chloride (98-59-9) + (2S,4S)-1-{2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4,5-dihydroxy-2-methyl-pentyl]-[1,3]dithian-2-yl}-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,4-diol → 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)

Guidance literature:

With dmap; 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)-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)

Guidance literature:

Multi-step reaction with 8 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

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

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

upstream raw materials:

p-toluenesulfonyl chloride

(R)-2,2-Dimethyl-4-((S)-2-methyl-oxiranylmethyl)-[1,3]dioxolane

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

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

C₄₈H₇₄O₈S₃Si₂

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

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