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

Base Information

• Chemical Name: (R)-2-((2S,5S,7S)-2-{(S)-[(2R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide
• CAS No.: 499992-30-2
• Molecular Formula: C₃₈H₅₇NO₈Si
• Molecular Weight: 683.958

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

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Useful:

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

There total 18 articles about (R)-2-((2S,5S,7S)-2-{(S)-[(2R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-2-methyl-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: 72.0%

Thiocarbonic acid O-[(2S,4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-{(S)-hydroxy-[(2S,5S,7S)-7-((R)-1-phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]dec-2-yl]-methyl}-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-ylmethyl] ester O-phenyl ester (499992-29-9) → (R)-2-((2S,5S,7S)-2-{(S)-[(2R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide (499992-30-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In xylene; at 160 ℃;

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

Reference yield:

(S)-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-D-glyceraldehyde (98944-53-7) → (R)-2-((2S,5S,7S)-2-{(S)-[(2R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide (499992-30-2)

Guidance literature:

Multi-step reaction with 8 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

7.1: 75 percent / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / -10 °C

8.1: 72 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / xylene / 160 °C

With tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; titanium(IV) trichloride isopropoxide; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; tert.-butyl lithium; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; lithium 4,4′-di-tert-butylbiphenylide; In tetrahydrofuran; diethyl ether; dichloromethane; xylene; benzene; 8.1: Barton deoxygenation;

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

Reference yield:

(2R,3S)-3-Hydroxy-2-methyl-oct-7-enoic acid phenylamide (499992-07-3) → (R)-2-((2S,5S,7S)-2-{(S)-[(2R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide (499992-30-2)

Guidance literature:

Multi-step reaction with 12 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

11.1: 75 percent / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / -10 °C

12.1: 72 percent / Bu₃SnH; 2,2'-azobisisobutyronitrile / xylene / 160 °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; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; xylene; pentane; benzene; 3.1: Wittig coupling / 12.1: Barton deoxygenation;

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

upstream raw materials:

Thiocarbonic acid O-[(2S,4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-{(S)-hydroxy-[(2S,5S,7S)-7-((R)-1-phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]dec-2-yl]-methyl}-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-ylmethyl] ester O-phenyl ester

(S)-2-O-benzyl-3-O-(tert-butyldimethylsilyl)-D-glyceraldehyde

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

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

Downstream 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-((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

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