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

Base Information

• Chemical Name: 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
• CAS No.: 499992-29-9
• Molecular Formula: C₄₅H₆₁NO₁₀SSi
• Molecular Weight: 836.132

Synonyms: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

Chemical Property of 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

Chemical Property:

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Safty Information:

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Technology Process of 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

There total 17 articles about 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 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: 75.0%

phenylcarbonochloridothioate (1005-56-7) + (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 (499992-20-0) → 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)

Guidance literature:

With dmap; In dichloromethane; at -10 ℃;

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) → 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)

Guidance literature:

Multi-step reaction with 7 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

With tert.-butylhydroperoxide; dmap; 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:

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

Guidance literature:

Multi-step reaction with 10 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

With tert.-butylhydroperoxide; dmap; 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; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; pentane; benzene; 2.1: Wittig coupling;

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

upstream raw materials:

phenylcarbonochloridothioate

(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

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

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

Downstream raw materials:

(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

(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)-[(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

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