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

Base Information

Chemical Name:(2S,4S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-4-methyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol
CAS No.:868266-94-8
Molecular Formula:C₃₁H₅₂O₇Si
Molecular Weight:564.835
Hs Code.:

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

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

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

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

There total 8 articles about (2S,4S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-4-methyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol 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: 94.0%

: 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

: 917-54-4
methyllithium

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

: 868266-94-8
(2S,4S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-4-methyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol

Guidance literature:: With cerium(III) chloride; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1002/anie.200502008

Reference yield:

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

: 868266-94-8
(2S,4S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-4-methyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol

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: 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

With 1H-imidazole; perchloric acid; cerium(III) chloride; 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

: 868266-94-8
(2S,4S,6S,8R,10S)-2-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-8-(4-methoxy-benzyloxymethyl)-4-methyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; cerium(III) chloride; iodine; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1002/anie.200502008