Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester
• CAS No.: 868266-95-9
• Molecular Formula: C₃₀H₅₀O₈SSi
• Molecular Weight: 598.874

Synonyms:Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester

There total 10 articles about Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-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: 97.0%

(2S,4S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-hydroxymethyl-4-methyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol (868267-05-4) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (868266-95-9)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 19h;

DOI:10.1002/anie.200502008

Reference yield:

2-(1-methyl-2-triethylsilanyloxy-ethyl)-4-triethylsilanyloxy-hept-1-en-6-yne → Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (868266-95-9)

Guidance literature:

Multi-step reaction with 9 steps

1: i-PrMgCl / tetrahydrofuran / 1 h / -20 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3: 97 percent / NaOMe / methanol; CH₂Cl₂ / 16 h / -10 - 20 °C

4: aq. HClO₄ / acetonitrile; CH₂Cl₂ / 0.5 h / 20 °C

5: 94 percent / imidazole / CH₂Cl₂ / 17 h / 20 °C

6: 99 percent / I₂; aq. NaHCO₃ / acetonitrile / 1 h / 0 °C

7: 94 percent / CeCl₃ / tetrahydrofuran / 1 h / -78 °C

8: 98 percent / DDQ; aq. pH 7 buffer / CH₂Cl₂ / 2 h / 20 °C / pH 7

9: 97 percent / pyridine / CH₂Cl₂ / 19 h / 20 °C

With pyridine; 1H-imidazole; perchloric acid; cerium(III) chloride; pH 7 buffer; iodine; isopropylmagnesium chloride; sodium methylate; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2: Dess-Martin oxidation;

DOI:10.1002/anie.200502008

Reference yield:

(8S,10R,12S,15S)-15-((R)-4-Hydroxy-3-methyl-2-methylene-butyl)-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol (868266-89-1) → Toluene-4-sulfonic acid (2R,4S,6S,8S,10S)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-4,10-dihydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester (868266-95-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / imidazole / CH₂Cl₂ / 17 h / 20 °C

2: 99 percent / I₂; aq. NaHCO₃ / acetonitrile / 1 h / 0 °C

3: 94 percent / CeCl₃ / tetrahydrofuran / 1 h / -78 °C

4: 98 percent / DDQ; aq. pH 7 buffer / CH₂Cl₂ / 2 h / 20 °C / pH 7

5: 97 percent / pyridine / CH₂Cl₂ / 19 h / 20 °C

With pyridine; 1H-imidazole; cerium(III) chloride; pH 7 buffer; iodine; sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/anie.200502008

upstream raw materials:

(2S,4S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-hydroxymethyl-4-methyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol

p-toluenesulfonyl chloride

(8S,10R,12S,15S)-15-((R)-4-Hydroxy-3-methyl-2-methylene-butyl)-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol

(2S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-hydroxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one

Downstream raw materials:

C₅₈H₉₆O₁₅Si₂

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