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

Base Information

• Chemical Name: (2R,6S,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one
• CAS No.: 868266-99-3
• Molecular Formula: C₃₆H₆₂O₇Si₂
• Molecular Weight: 663.055

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

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

Chemical Property:

Purity/Quality:

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

There total 9 articles about (2R,6S,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one 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:

(2R,6S,8R,10S)-10-Hydroxy-2-((R)-4-hydroxy-3-methyl-2-methylene-butyl)-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one + tert-butyldimethylsilyl chloride (18162-48-6) → (2R,6S,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one (868266-99-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 14h;

DOI:10.1002/anie.200502008

Reference yield:

2-(1-methyl-2-triethylsilanyloxy-ethyl)-4-triethylsilanyloxy-hept-1-en-6-yne → (2R,6S,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one (868266-99-3)

Guidance literature:

Multi-step reaction with 7 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: PhI(Tfa)2 / 0.67 h / 0 °C

6: aq. NaHCO₃; AcOH / tetrahydrofuran / 6 h / 30 °C

7: imidazole / dimethylformamide / 14 h / 20 °C

With 1H-imidazole; perchloric acid; isopropylmagnesium chloride; sodium methylate; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2: Dess-Martin oxidation;

DOI:10.1002/anie.200502008

Reference yield:

1-[6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(1-methyl-2-triethylsilanyloxy-ethyl)-6-triethylsilanyloxy-non-8-en-3-yn-2-ol (868267-04-3) → (2R,6S,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecan-4-one (868266-99-3)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 97 percent / NaOMe / methanol; CH₂Cl₂ / 16 h / -10 - 20 °C

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

4: PhI(Tfa)2 / 0.67 h / 0 °C

5: aq. NaHCO₃; AcOH / tetrahydrofuran / 6 h / 30 °C

6: imidazole / dimethylformamide / 14 h / 20 °C

With 1H-imidazole; perchloric acid; sodium methylate; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Dess-Martin oxidation;

DOI:10.1002/anie.200502008

upstream raw materials:

tert-butyldimethylsilyl chloride

(8S,10R,12S,15R)-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

(8R,10R,12S,15R)-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

1-[6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(1-methyl-2-triethylsilanyloxy-ethyl)-6-triethylsilanyloxy-non-8-en-3-yn-2-one

Downstream raw materials:

C₅₈H₉₆O₁₅Si₂

C₄₁H₆₉BO₇Si

1-[(2S,4S,6R,8R,10S)-10-(tert-butyldimethylsilanyloxy)-4-methoxy-8-(p-methoxybenzyloxymethyl)-1,7-dioxaspiro[5.5]undec-2-yl]butan-2-one

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

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