3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester

Base Information

• Chemical Name: 3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester
• CAS No.: 931113-66-5
• Molecular Formula: C₃₄H₄₈O₇Si
• Molecular Weight: 596.836

Synonyms:3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester

Chemical Property of 3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester

There total 20 articles about 3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl 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: 80.0%

(E)-3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-acrylic acid methyl ester → 3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester (931113-66-5)

Guidance literature:

With phenylsilane; oxygen; bis(dipivaloylmethanato)manganese(II); In 1,2-dichloro-ethane; isopropyl alcohol; under 760 Torr;

DOI:10.1021/ol0504291

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester (931113-66-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 70 percent / Ag₂O

2.1: AlMe₃ / CH₂Cl₂; hexane / 0.33 h / 0 °C

3.1: 1.14 g / camphorsulfonic acid / CH₂Cl₂ / 20 °C

4.1: tert-butyllithium / pentane; diethyl ether / 1.17 h / -78 - 0 °C

4.2: 72 percent / pentane; diethyl ether / 3 h / 0 °C

5.1: 92 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 20 °C / pH 7

6.1: 95 percent / liithium p,p'-di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

7.1: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h

8.1: 86 percent / CH₂Cl₂ / 2 h / 20 °C

9.1: 89 percent / Dibal-H / CH₂Cl₂; hexane / 1 h / -40 °C

10.1: 95 percent / molecular sieves 4 Angstroem; L-(+)-diethyl tartrate; titanium isopropoxide / tert-butyl hydroperoxide / CH₂Cl₂ / 12 h / -23 °C

11.1: 98 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

12.1: 86 percent / CH₂Cl₂ / 24 h / 20 °C

13.1: 80 percent / phenylsilane; O₂ / bis(dipivaloylmethanato)manganese(III) complex / 1,2-dichloro-ethane; propan-2-ol / 760 Torr

With pyridine; titanium(IV) isopropylate; lithium 4,4′-di(tert-butyl)biphenyl; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; phenylsilane; trimethylaluminum; tert.-butyl lithium; oxygen; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; tert.-butylhydroperoxide; bis(dipivaloylmethanato)manganese(II); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; isopropyl alcohol; pentane; 8.1: Wittig reaction / 12.1: Wittig reaction;

DOI:10.1021/ol0504291

Reference yield:

(S)-5-Benzyloxy-4-hydroxy-pentanoic acid methoxy-methyl-amide (852245-14-8) → 3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester (931113-66-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 1.14 g / camphorsulfonic acid / CH₂Cl₂ / 20 °C

2.1: tert-butyllithium / pentane; diethyl ether / 1.17 h / -78 - 0 °C

2.2: 72 percent / pentane; diethyl ether / 3 h / 0 °C

3.1: 92 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 20 °C / pH 7

4.1: 95 percent / liithium p,p'-di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

5.1: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h

6.1: 86 percent / CH₂Cl₂ / 2 h / 20 °C

7.1: 89 percent / Dibal-H / CH₂Cl₂; hexane / 1 h / -40 °C

8.1: 95 percent / molecular sieves 4 Angstroem; L-(+)-diethyl tartrate; titanium isopropoxide / tert-butyl hydroperoxide / CH₂Cl₂ / 12 h / -23 °C

9.1: 98 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

10.1: 86 percent / CH₂Cl₂ / 24 h / 20 °C

11.1: 80 percent / phenylsilane; O₂ / bis(dipivaloylmethanato)manganese(III) complex / 1,2-dichloro-ethane; propan-2-ol / 760 Torr

With pyridine; titanium(IV) isopropylate; lithium 4,4′-di(tert-butyl)biphenyl; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; phenylsilane; tert.-butyl lithium; oxygen; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert.-butylhydroperoxide; bis(dipivaloylmethanato)manganese(II); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; isopropyl alcohol; pentane; 6.1: Wittig reaction / 10.1: Wittig reaction;

DOI:10.1021/ol0504291

upstream raw materials:

(S)-5-Benzyloxy-4-hydroxy-pentanoic acid methoxy-methyl-amide

(S)-5-Benzyloxy-4-(4-methoxy-benzyloxy)-pentanoic acid methoxy-methyl-amide

(2S,3S)-6-Benzyloxy-3-(4-methoxy-benzyloxy)-2-methyl-hexan-1-ol

(4R,5S)-3-((2R,3S)-6-Benzyloxy-3-hydroxy-2-methyl-hexanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Downstream raw materials:

C₄₀H₆₂O₇Si₂

C₇₅H₁₀₆O₁₁Si₂

C₆₉H₉₂O₁₁Si

C₇₅H₁₀₆O₁₁Si₂

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