(2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic acid methyl ester
• CAS No.: 883142-64-1
• Molecular Formula: C₃₄H₄₇NO₅Si
• Molecular Weight: 577.836

Synonyms:(2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic acid methyl ester

Chemical Property of (2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic acid methyl ester

There total 19 articles about (2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic 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:

(R)-2-(Tetrahydro-pyran-2-yloxymethyl)-pentanal → (2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic acid methyl ester (883142-64-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: n-BuLi

1.2: tetrahydrofuran / 0 - 20 °C

2.1: (DHQD)2PYR; K₂OsO₄; aq. K₂CO₃ / K₃Fe(CN)6 / 2-methyl-propan-2-ol / 0 h

3.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

4.1: Et₃N / CH₂Cl₂ / 0 °C

5.1: NaN₃ / dimethylformamide / 80 °C

6.1: PPTS / ethanol / 60 °C

7.1: NaH / tetrahydrofuran / 0 - 20 °C

8.1: 60 percent / H₂ / Pd/C / ethyl acetate / 760 Torr

9.1: LiHMDS / tetrahydrofuran

9.2: 94 percent / tetrahydrofuran / -78 - -40 °C

10.1: 81 percent / Et₃N / Pd(Ph₃P)4 / dimethylformamide / 75 °C

11.1: 96 percent / diethyl ether / -78 - -10 °C

12.1: 95 percent / Super-Hydride(R) / tetrahydrofuran / 0 °C

13.1: NaH / tetrahydrofuran / 0 - 20 °C

With dmap; potassium osmate(VI); n-butyllithium; sodium azide; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; lithium triethylborohydride; potassium carbonate; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation / 7.1: Swern oxidation / 8.1: Horner-Emmons reaction / 14.1: Swern oxidation;

DOI:10.1055/s-2005-921911

Reference yield:

2-(2-propyl-but-3-enyloxy)-tetrahydro-pyran (883142-56-1) → (2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic acid methyl ester (883142-64-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: (DHQD)2PYR; K₂OsO₄; aq. K₂CO₃ / K₃Fe(CN)6 / 2-methyl-propan-2-ol / 0 h

2.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

3.1: Et₃N / CH₂Cl₂ / 0 °C

4.1: NaN₃ / dimethylformamide / 80 °C

5.1: PPTS / ethanol / 60 °C

6.1: NaH / tetrahydrofuran / 0 - 20 °C

7.1: 60 percent / H₂ / Pd/C / ethyl acetate / 760 Torr

8.1: LiHMDS / tetrahydrofuran

8.2: 94 percent / tetrahydrofuran / -78 - -40 °C

9.1: 81 percent / Et₃N / Pd(Ph₃P)4 / dimethylformamide / 75 °C

10.1: 96 percent / diethyl ether / -78 - -10 °C

11.1: 95 percent / Super-Hydride(R) / tetrahydrofuran / 0 °C

12.1: NaH / tetrahydrofuran / 0 - 20 °C

With dmap; potassium osmate(VI); sodium azide; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; lithium triethylborohydride; potassium carbonate; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 6.1: Swern oxidation / 7.1: Horner-Emmons reaction / 13.1: Swern oxidation;

DOI:10.1055/s-2005-921911

Reference yield:

(S)-2-(Tetrahydro-pyran-2-yloxymethyl)-pentan-1-ol → (2S,3R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((E)-2-ethoxycarbonyl-vinyl)-3-propyl-5-vinyl-piperidine-1-carboxylic acid methyl ester (883142-64-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: n-BuLi

1.2: tetrahydrofuran / 0 - 20 °C

2.1: (DHQD)2PYR; K₂OsO₄; aq. K₂CO₃ / K₃Fe(CN)6 / 2-methyl-propan-2-ol / 0 h

3.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

4.1: Et₃N / CH₂Cl₂ / 0 °C

5.1: NaN₃ / dimethylformamide / 80 °C

6.1: PPTS / ethanol / 60 °C

7.1: NaH / tetrahydrofuran / 0 - 20 °C

8.1: 60 percent / H₂ / Pd/C / ethyl acetate / 760 Torr

9.1: LiHMDS / tetrahydrofuran

9.2: 94 percent / tetrahydrofuran / -78 - -40 °C

10.1: 81 percent / Et₃N / Pd(Ph₃P)4 / dimethylformamide / 75 °C

11.1: 96 percent / diethyl ether / -78 - -10 °C

12.1: 95 percent / Super-Hydride(R) / tetrahydrofuran / 0 °C

13.1: NaH / tetrahydrofuran / 0 - 20 °C

With dmap; potassium osmate(VI); n-butyllithium; sodium azide; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; lithium triethylborohydride; potassium carbonate; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Swern oxidation / 3.1: Sharpless asymmetric dihydroxylation / 8.1: Swern oxidation / 9.1: Horner-Emmons reaction / 15.1: Swern oxidation;

DOI:10.1055/s-2005-921911

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

2-(2-propyl-but-3-enyloxy)-tetrahydro-pyran

(5R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-propyl-piperidin-2-one

(E)-(R)-4-[(S)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-hept-2-enoic acid ethyl ester

Downstream raw materials:

(2S,3R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-ethyl-6-(3-hydroxy-propyl)-3-propyl-piperidine-1-carboxylic acid methyl ester

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