[(2R,4S,6S,8S,10S)-8-[(2S,3R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-hydroxy-3-methyl-4-oxo-butyl]-4-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl ester

Base Information

• Chemical Name: [(2R,4S,6S,8S,10S)-8-[(2S,3R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-hydroxy-3-methyl-4-oxo-butyl]-4-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl ester
• CAS No.: 251641-31-3
• Molecular Formula: C₃₇H₅₉NO₁₀Si
• Molecular Weight: 705.962

Synonyms:

Chemical Property of [(2R,4S,6S,8S,10S)-8-[(2S,3R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-hydroxy-3-methyl-4-oxo-butyl]-4-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of [(2R,4S,6S,8S,10S)-8-[(2S,3R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-hydroxy-3-methyl-4-oxo-butyl]-4-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl ester

There total 13 articles about [(2R,4S,6S,8S,10S)-8-[(2S,3R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-hydroxy-3-methyl-4-oxo-butyl]-4-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl 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:

(2S,4S,6R,8S,10S)-2,8-Bis-(2-benzyloxy-ethyl)-4-methyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol → [(2R,4S,6S,8S,10S)-8-[(2S,3R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-hydroxy-3-methyl-4-oxo-butyl]-4-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl ester (251641-31-3)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N / CH₂Cl₂

2: 100 percent / H₂ / Pd(OH)2/C / ethyl acetate

3: 72 percent / LDA / tetrahydrofuran

4: 100 percent / Dess-Martin periodinane

5: aq. camphorsulfonic acid / tetrahydrofuran

6: NaClO₂

7: CH₂Cl₂

8: 100 percent / Dess-Martin periodinane

9: Bu₂BOTf; Et₃N

With sodium chlorite; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: silylation / 2: Hydrogenation / 3: Metallation / 3: silylation / 4: Oxidation / 5: desilylation / 6: Oxidation / 7: Esterification / 8: Oxidation / 9: Addition / 9: Condensation;

DOI:10.1021/jo9910987

Reference yield:

(2S,4S,6R,8S,10S)-2,8-Bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-4-methyl-1,7-dioxa-spiro[5.5]undecan-4-ol (185409-89-6) → [(2R,4S,6S,8S,10S)-8-[(2S,3R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-hydroxy-3-methyl-4-oxo-butyl]-4-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl ester (251641-31-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / H₂ / Pd(OH)2/C / ethyl acetate

2: 72 percent / LDA / tetrahydrofuran

3: 100 percent / Dess-Martin periodinane

4: aq. camphorsulfonic acid / tetrahydrofuran

5: NaClO₂

6: CH₂Cl₂

7: 100 percent / Dess-Martin periodinane

8: Bu₂BOTf; Et₃N

With sodium chlorite; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: Hydrogenation / 2: Metallation / 2: silylation / 3: Oxidation / 4: desilylation / 5: Oxidation / 6: Esterification / 7: Oxidation / 8: Addition / 8: Condensation;

DOI:10.1021/jo9910987

Reference yield:

(2S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-1,7-dioxa-spiro[5.5]undecane-4,10-dione → [(2R,4S,6S,8S,10S)-8-[(2S,3R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-hydroxy-3-methyl-4-oxo-butyl]-4-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl ester (251641-31-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide

1.2: 64 percent / hexane

2.1: 94 percent / L-selectride / tetrahydrofuran

3.1: 94 percent / TBAF*3H₂O / tetrahydrofuran / -78 °C

4.1: CeCl₃ / tetrahydrofuran

5.1: Et₃N / CH₂Cl₂

6.1: 100 percent / H₂ / Pd(OH)2/C / ethyl acetate

7.1: 72 percent / LDA / tetrahydrofuran

8.1: 100 percent / Dess-Martin periodinane

9.1: aq. camphorsulfonic acid / tetrahydrofuran

10.1: NaClO₂

11.1: CH₂Cl₂

12.1: 100 percent / Dess-Martin periodinane

13.1: Bu₂BOTf; Et₃N

With sodium chlorite; cerium(III) chloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; L-Selectride; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; 1.1: Metallation / 1.2: silylation / 2.1: Reduction / 3.1: desilylation / 4.1: Addition / 5.1: silylation / 6.1: Hydrogenation / 7.1: Metallation / 7.2: silylation / 8.1: Oxidation / 9.1: desilylation / 10.1: Oxidation / 11.1: Esterification / 12.1: Oxidation / 13.1: Addition / 13.2: Condensation;

DOI:10.1021/jo9910987

upstream raw materials:

(3R)-3-propionyl-4-benzyloxazolidin-2-one

[(2R,4S,6S,8R,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-8-(2-oxo-ethyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl ester

(2S,4S,6R,8S,10S)-2,8-Bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-4-methyl-1,7-dioxa-spiro[5.5]undecan-4-ol

(2S,4S,6R,8S,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-2,8-bis-(2-hydroxy-ethyl)-4-methyl-1,7-dioxa-spiro[5.5]undecan-4-ol

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