(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

Base Information

Chemical Name:(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
CAS No.:868266-93-7
Molecular Formula:C₃₀H₄₈O₇Si
Molecular Weight:548.792
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 99.0%

: 868266-92-6
(8S,10R,12S,15S)-15-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-(4-methoxy-benzyloxymethyl)-9,14-dioxa-1,5-dithia-dispiro[5.1.5.3]hexadecan-12-ol

: 868266-93-7
(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

Guidance literature:: With iodine; sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 1h;
DOI:10.1002/anie.200502008

Reference yield:

: 2-(1-methyl-2-triethylsilanyloxy-ethyl)-4-triethylsilanyloxy-hept-1-en-6-yne

: 868266-93-7
(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

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; perchloric acid; iodine; isopropylmagnesium chloride; sodium methylate; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2: Dess-Martin oxidation;
DOI:10.1002/anie.200502008

Reference yield:

: 868266-89-1
(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

: 868266-93-7
(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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With 1H-imidazole; iodine; sodium hydrogencarbonate; In dichloromethane; acetonitrile;
DOI:10.1002/anie.200502008