(R)-2-((2S,5S,7S)-2-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

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Chemical Name:(R)-2-((2S,5S,7S)-2-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide
CAS No.:499992-20-0
Molecular Formula:C₃₈H₅₇NO₉Si
Molecular Weight:699.957
Hs Code.:

(R)-2-((2S,5S,7S)-2-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

Synonyms:(R)-2-((2S,5S,7S)-2-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-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-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-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-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

There total 16 articles about (R)-2-((2S,5S,7S)-2-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-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: 87.0%

: (R)-2-[(2S,5S,7S)-2-((S)-{2-[(2R,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-(4-methoxy-benzyloxy)-butyl]-oxiranyl}-hydroxy-methyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-N-phenyl-propionamide

: 499992-20-0
(R)-2-((2S,5S,7S)-2-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane;
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

: 499992-20-0
(R)-2-((2S,5S,7S)-2-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

Guidance literature:: Multi-step reaction with 6 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 / -78 °C

3.2: 68 percent / MgBr₂ / diethyl ether; benzene / -78 °C

4.1: 81 percent / lithium di-tert-butyl biphenylide / tetrahydrofuran / -78 °C

5.1: 99 percent / [VO(acac)2]; tert-butyl hydroperoxide / benzene

6.1: 87 percent / pyridinium para-toluenesulfonate / CH₂Cl₂

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; tert.-butyl lithium; pyridinium p-toluenesulfonate; lithium 4,4′-di-tert-butylbiphenylide; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V

Reference yield:

: 499992-07-3
(2R,3S)-3-Hydroxy-2-methyl-oct-7-enoic acid phenylamide

: 499992-20-0
(R)-2-((2S,5S,7S)-2-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: O₃ / methanol

1.2: dimethylsulfide / methanol / -78 °C

1.3: 96 percent / camphorsulfonic acid

2.1: acetonitrile / 60 °C

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

4.1: camphorsulfonic acid / methanol; CH₂Cl₂

5.1: 91 percent / i-PrMgCl / tetrahydrofuran / -78 - -20 °C

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

6.2: 94 percent / diethyl ether; pentane

7.1: LiBHBu₃

8.1: 81 percent / lithium di-tert-butyl biphenylide / tetrahydrofuran / -78 °C

9.1: 99 percent / [VO(acac)2]; tert-butyl hydroperoxide / benzene

10.1: 87 percent / pyridinium para-toluenesulfonate / CH₂Cl₂

With tert.-butylhydroperoxide; n-butyllithium; bis(acetylacetonate)oxovanadium; camphor-10-sulfonic acid; tert.-butyl lithium; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; LiHB(s-Bu)3; lithium 4,4′-di-tert-butylbiphenylide; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; pentane; benzene; 3.1: Wittig coupling;
DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V