Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-oxo-octyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-oxo-octyl ester
• CAS No.: 204572-70-3
• Molecular Formula: C₄₅H₉₀O₉SSi₄
• Molecular Weight: 919.612

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-oxo-octyl ester

Chemical Property:

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MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-oxo-octyl ester

There total 9 articles about Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-oxo-octyl 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: 90.0%

Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-hydroxy-octyl ester (204572-69-0) → Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-oxo-octyl ester (204572-70-3)

Guidance literature:

With Dess-Martin periodane;

DOI:10.1016/S0040-4039(97)10739-0

Reference yield:

(R)-5-((R)-4-Benzyloxy-1-hydroxy-butyl)-dihydro-furan-2-one (181803-09-8) → Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-oxo-octyl ester (204572-70-3)

Guidance literature:

Multi-step reaction with 7 steps

2: imidazole

3: DIBAL-H

4: 86 percent / InCl₃

5: 72 percent / pyridine

6: 89 percent / H₂ / Pd-C

7: 90 percent / Dess-Martin reagent

With 1H-imidazole; indium(III) chloride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; palladium on activated charcoal; In pyridine;

DOI:10.1016/S0040-4039(97)10739-0

Reference yield:

(E)-8-Benzyloxy-oct-4-enoic acid methyl ester → Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-oxo-octyl ester (204572-70-3)

Guidance literature:

Multi-step reaction with 9 steps

1: AD-Mix-β

2: AlMe₃

4: imidazole

5: DIBAL-H

6: 86 percent / InCl₃

7: 72 percent / pyridine

8: 89 percent / H₂ / Pd-C

9: 90 percent / Dess-Martin reagent

With 1H-imidazole; indium(III) chloride; AD-mix-β; hydrogen; trimethylaluminum; diisobutylaluminium hydride; Dess-Martin periodane; palladium on activated charcoal; In pyridine;

DOI:10.1016/S0040-4039(97)10739-0

upstream raw materials:

Toluene-4-sulfonic acid (1S,4R,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-8-hydroxy-octyl ester

(R)-5-((R)-4-Benzyloxy-1-hydroxy-butyl)-dihydro-furan-2-one

(4R,5R)-8-Benzyloxy-4,5-dihydroxy-octanoic acid methyl ester

(4R,5R)-8-Benzyloxy-4,5-dihydroxy-octanoic acid methoxy-amide

Downstream raw materials:

C₆₄H₁₃₀O₁₃SSi₅

C₇₁H₁₃₆O₁₅S₂Si₅

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