(R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde

Base Information

• Chemical Name: (R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde
• CAS No.: 152192-49-9
• Molecular Formula: C₂₅H₄₂O₄Si
• Molecular Weight: 434.692
• Mol file: 152192-49-9.mol

Synonyms:(R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde

Chemical Property of (R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde

There total 8 articles about (R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde 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: 92.0%

(S)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propan-1-ol (152192-52-4) → (R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde (152192-49-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) up to RT;

DOI:10.1016/S0040-4039(00)73994-3

Reference yield:

2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester (860478-32-6) → (R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde (152192-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / 2,6-lutidine / CH₂Cl₂ / 66 h / 30 °C

2: 92 percent / DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

3: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 3: Swern oxidation;

DOI:10.1021/ol050864v

Reference yield:

2,2-Dimethyl-propionic acid (S)-2-[(4S,5R,6S)-6-((S)-2-benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propyl ester (860295-66-5) → (R)-2-[(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propionaldehyde (152192-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

2: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 2: Swern oxidation;

DOI:10.1021/ol050864v

upstream raw materials:

(S)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propan-1-ol

2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester

2,2-Dimethyl-propionic acid (S)-2-[(4S,5R,6S)-6-((S)-2-benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propyl ester

2,2-Dimethyl-propionic acid (2S,3S,4S,5S,6S)-7-benzyloxy-3-hydroxy-2,4,6-trimethyl-5-triethylsilanyloxy-heptyl ester

Downstream raw materials:

(4S,5S,6S)-4-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-6-((S)-3,3-dibromo-1-methyl-allyl)-5-methyl-[1,3,2]dioxasilinane

(4S,5S,6S)-4-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-6-((S)-1-methyl-prop-2-ynyl)-[1,3,2]dioxasilinane

(4S,5S,6S)-4-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-6-[(S)-3-((2R,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-1-methyl-prop-2-ynyl]-5-methyl-[1,3,2]dioxasilinane

(E)-(2S,6R,7R,8R)-2-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-triisopropylsilanyloxy-dec-3-en-5-one