2-[(1S,2S,3S,5S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-{(3Z)-4-[dimethyl(phenyl)silyl]-3-(trimethylstannanyl)but-3-enoyl}-5-(methoxymethoxy)-3-methylcyclopentyl]prop-2-enal

Base Information

• Chemical Name: 2-[(1S,2S,3S,5S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-{(3Z)-4-[dimethyl(phenyl)silyl]-3-(trimethylstannanyl)but-3-enoyl}-5-(methoxymethoxy)-3-methylcyclopentyl]prop-2-enal
• CAS No.: 1586810-09-4
• Molecular Formula: C₃₂H₅₄O₅Si₂Sn
• Molecular Weight: 693.659
• Mol file: 1586810-09-4.mol

Synonyms:2-[(1S,2S,3S,5S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-{(3Z)-4-[dimethyl(phenyl)silyl]-3-(trimethylstannanyl)but-3-enoyl}-5-(methoxymethoxy)-3-methylcyclopentyl]prop-2-enal

Chemical Property of 2-[(1S,2S,3S,5S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-{(3Z)-4-[dimethyl(phenyl)silyl]-3-(trimethylstannanyl)but-3-enoyl}-5-(methoxymethoxy)-3-methylcyclopentyl]prop-2-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1S,2S,3S,5S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-{(3Z)-4-[dimethyl(phenyl)silyl]-3-(trimethylstannanyl)but-3-enoyl}-5-(methoxymethoxy)-3-methylcyclopentyl]prop-2-enal

There total 6 articles about 2-[(1S,2S,3S,5S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-{(3Z)-4-[dimethyl(phenyl)silyl]-3-(trimethylstannanyl)but-3-enoyl}-5-(methoxymethoxy)-3-methylcyclopentyl]prop-2-enal 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: 100.0%

(1S,2S,4S,5R,6S)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-{(2Z)-3-[dimethyl(phenyl)silyl]-2-(trimethylstannanyl)prop-2-en-1-yl}-7,7-bis-(hydroxymethyl)-2-(methoxymethoxy)-4-methylbicyclo[3.2.0]heptan-6-ol (1586810-08-3) → 2-[(1S,2S,3S,5S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-{(3Z)-4-[dimethyl(phenyl)silyl]-3-(trimethylstannanyl)but-3-enoyl}-5-(methoxymethoxy)-3-methylcyclopentyl]prop-2-enal (1586810-09-4)

Guidance literature:

(1S,2S,4S,5R,6S)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-{(2Z)-3-[dimethyl(phenyl)silyl]-2-(trimethylstannanyl)prop-2-en-1-yl}-7,7-bis-(hydroxymethyl)-2-(methoxymethoxy)-4-methylbicyclo[3.2.0]heptan-6-ol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h;

With triethylamine; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1002/ejoc.201300870

Reference yield:

C31H64O5Si3 (1373502-48-7) → 2-[(1S,2S,3S,5S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-{(3Z)-4-[dimethyl(phenyl)silyl]-3-(trimethylstannanyl)but-3-enoyl}-5-(methoxymethoxy)-3-methylcyclopentyl]prop-2-enal (1586810-09-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0.5 h / 0 °C

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C

3.1: pyridinium p-toluenesulfonate / acetone / 0 - 20 °C

4.1: dimethyl sulfoxide / 1 h / 50 °C

5.1: camphor-10-sulfonic acid / methanol / 1 h / 0 °C

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.75 h / 70 °C

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

7.2: 1 h / -78 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen fluoride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; 7.1: |Swern Oxidation;

DOI:10.1002/ejoc.201300870

Reference yield:

{(1R,2S,4S,5S)-2-[(tert-butyldimethylsilyl)oxy]-4-(methoxymethoxy)-2-methyl-7-methylenebicyclo[3.2.0]heptane-6,6-diyl}dimethanol → 2-[(1S,2S,3S,5S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-{(3Z)-4-[dimethyl(phenyl)silyl]-3-(trimethylstannanyl)but-3-enoyl}-5-(methoxymethoxy)-3-methylcyclopentyl]prop-2-enal (1586810-09-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C

2.1: pyridinium p-toluenesulfonate / acetone / 0 - 20 °C

3.1: dimethyl sulfoxide / 1 h / 50 °C

4.1: camphor-10-sulfonic acid / methanol / 1 h / 0 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.75 h / 70 °C

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

6.2: 1 h / -78 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; 6.1: |Swern Oxidation;

DOI:10.1002/ejoc.201300870

upstream raw materials:

tert-butyl{[(1'R,2'S,4'S,5'S,7'S)-4'-(methoxymethoxy)-2,2,2'-trimethyldispiro[1,3-dioxane-5,6'-bicyclo[3.2.0]heptane-7',2''-oxiran]-2'-yl]oxy}dimethylsilane

C₃₁H₆₄O₅Si₃

C₁₉H₃₆O₆Si

(1R,2S,4S,5S,7S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-(methoxymethoxy)-2,2,2-trimethyl-7-(prop-2-yn-1-yl)spiro[bicyclo[3.2.0]-heptane-6,5-[1,3]dioxan]-7-ol