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

Base Information

• Chemical Name: (R)-2-((2S,5S,7S)-2-{(S)-(tert-Butoxy-diphenyl-silanyloxy)-[(2R,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide
• CAS No.: 499992-22-2
• Molecular Formula: C₄₈H₆₁NO₉Si
• Molecular Weight: 824.099

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

Chemical Property of (R)-2-((2S,5S,7S)-2-{(S)-(tert-Butoxy-diphenyl-silanyloxy)-[(2R,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

Chemical Property:

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Technology Process of (R)-2-((2S,5S,7S)-2-{(S)-(tert-Butoxy-diphenyl-silanyloxy)-[(2R,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

There total 19 articles about (R)-2-((2S,5S,7S)-2-{(S)-(tert-Butoxy-diphenyl-silanyloxy)-[(2R,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-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: 85.0%

(R)-2-((2S,5S,7S)-2-{(S)-(tert-Butoxy-diphenyl-silanyloxy)-[(2R,4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide (499992-31-3) → (R)-2-((2S,5S,7S)-2-{(S)-(tert-Butoxy-diphenyl-silanyloxy)-[(2R,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide (499992-22-2)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; dichloromethane; at -20 ℃;

DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V

Reference yield:

(R)-2-((S)-6-Methoxy-tetrahydro-pyran-2-yl)-N-phenyl-propionamide (499992-08-4) → (R)-2-((2S,5S,7S)-2-{(S)-(tert-Butoxy-diphenyl-silanyloxy)-[(2R,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide (499992-22-2)

Guidance literature:

Multi-step reaction with 13 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

6.1: LiBHBu₃

7.1: 81 percent / lithium di-tert-butyl biphenylide / tetrahydrofuran / -78 °C

8.1: 99 percent / [VO(acac)2]; tert-butyl hydroperoxide / benzene

9.1: 87 percent / pyridinium para-toluenesulfonate / CH₂Cl₂

10.1: 75 percent / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / -10 °C

11.1: 72 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / xylene / 160 °C

12.1: 90 percent / 4-(N,N-dimethylamino)pyridine; triethylamine / dimethylformamide

13.1: 85 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / -20 °C

With tert.-butylhydroperoxide; dmap; n-butyllithium; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tert.-butyl lithium; isopropylmagnesium chloride; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; LiHB(s-Bu)3; lithium 4,4′-di-tert-butylbiphenylide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; xylene; pentane; benzene; 2.1: Wittig coupling / 11.1: Barton deoxygenation;

DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V

Reference yield:

2-benzyloxy-5-bromo-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol → (R)-2-((2S,5S,7S)-2-{(S)-(tert-Butoxy-diphenyl-silanyloxy)-[(2R,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide (499992-22-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 79 percent / trifluoromethanesulfonic acid / diethyl ether / -20 - 0 °C

2.1: t-BuLi / diethyl ether / -78 °C

2.2: 68 percent / MgBr₂ / diethyl ether; benzene / -78 °C

3.1: 81 percent / lithium di-tert-butyl biphenylide / tetrahydrofuran / -78 °C

4.1: 99 percent / [VO(acac)2]; tert-butyl hydroperoxide / benzene

5.1: 87 percent / pyridinium para-toluenesulfonate / CH₂Cl₂

6.1: 75 percent / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / -10 °C

7.1: 72 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / xylene / 160 °C

8.1: 90 percent / 4-(N,N-dimethylamino)pyridine; triethylamine / dimethylformamide

9.1: 85 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / -20 °C

With tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; camphor-10-sulfonic acid; tert.-butyl lithium; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; lithium 4,4′-di-tert-butylbiphenylide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; xylene; benzene; 7.1: Barton deoxygenation;

DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V

upstream raw materials:

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

(R)-2-((S)-6-Methoxy-tetrahydro-pyran-2-yl)-N-phenyl-propionamide

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

(R)-2-((2S,5S,7S)-2-Formyl-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

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