(R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide

Base Information

Chemical Name:(R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide
CAS No.:499992-15-3
Molecular Formula:C₄₅H₆₁NO₈Si
Molecular Weight:772.067
Hs Code.:

(R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide

Synonyms:(R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide

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Chemical Property of (R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide

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Technology Process of (R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide

There total 9 articles about (R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide 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%

: 499992-12-0
(2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide

: [2-benzyloxy-5-bromo-3-(4-methoxy-benzyloxy)-hex-5-enyloxy]-tert-butyl-dimethyl-silane

: 499992-15-3
(R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide

Guidance literature:: [2-benzyloxy-5-bromo-3-(4-methoxy-benzyloxy)-hex-5-enyloxy]-tert-butyl-dimethyl-silane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃;

(2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide; In diethyl ether; pentane;
DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V

Reference yield:

: 98944-53-7
(S)-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-D-glyceraldehyde

: 499992-15-3
(R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / [Ti(OiPr)Cl₃] / CH₂Cl₂ / -78 °C

2.1: 79 percent / trifluoromethanesulfonic acid / diethyl ether / -20 - 0 °C

3.1: t-BuLi / diethyl ether; pentane / -78 °C

3.2: 94 percent / diethyl ether; pentane

With titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; tert.-butyl lithium; In diethyl ether; dichloromethane; pentane;
DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V

Reference yield:

: 499992-08-4
(R)-2-((S)-6-Methoxy-tetrahydro-pyran-2-yl)-N-phenyl-propionamide

: 499992-15-3
(R)-2-{(2S,5S,7S)-2-[(4R,5R)-5-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methylene-hexanoyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: acetonitrile / 60 °C

2.1: n-butyllithium / tetrahydrofuran / -78 °C

3.1: camphorsulfonic acid / methanol; CH₂Cl₂

4.1: 91 percent / i-PrMgCl / tetrahydrofuran / -78 - -20 °C

5.1: t-BuLi / diethyl ether; pentane / -78 °C

5.2: 94 percent / diethyl ether; pentane

With n-butyllithium; camphor-10-sulfonic acid; tert.-butyl lithium; isopropylmagnesium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; pentane; 2.1: Wittig coupling;
DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V