(R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid

Base Information

• Chemical Name: (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid
• CAS No.: 141566-35-0
• Molecular Formula: C₄₂H₇₆O₉Si₂
• Molecular Weight: 781.231
• Mol file: 141566-35-0.mol

Synonyms:

Chemical Property of (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid

There total 16 articles about (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid 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,5S,6R,7S,8S,9R)-9-Benzyloxymethoxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[(4S,5R,6R)-6-((S)-2-hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-6,8-dimethyl-decan-4-one → (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid (141566-35-0)

Guidance literature:

With potassium permanganate; In tert-butyl alcohol; at 20 ℃; for 0.5h; pH 7;

DOI:10.1016/S0040-4039(00)91728-3

Reference yield:

(2S,3S,4S,5R,6S)-7-hydroxy-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptyl p-toluenesulfonate (86534-97-6) → (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid (141566-35-0)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran / 3 h / 80 °C

2: NaIO₄ / methanol; H₂O / 21 h / 20 °C

3: 1.) LDA / 1,2-dimethoxy-ethane / 1.) -78 deg C, 15 min, 2.) -78 deg C, 15 min

4: H₂ / W-2 Ra Ni / diethyl ether / 1 h / 20 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -23 deg C, 30 min

6: KMnO₄ / 2-methyl-propan-2-ol / 0.5 h / 20 °C / pH 7

With potassium permanganate; sodium periodate; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; W-2 Ra Ni; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)91728-3

Reference yield:

(SRS,2S,3R,4S,5R,6R)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylsulfinyl)heptan-1-ol (86534-98-7) → (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid (141566-35-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1,2-dimethoxy-ethane / 1.) -78 deg C, 15 min, 2.) -78 deg C, 15 min

2: H₂ / W-2 Ra Ni / diethyl ether / 1 h / 20 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -23 deg C, 30 min

4: KMnO₄ / 2-methyl-propan-2-ol / 0.5 h / 20 °C / pH 7

With potassium permanganate; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; W-2 Ra Ni; In 1,2-dimethoxyethane; diethyl ether; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)91728-3

upstream raw materials:

(SRS,2S,3R,4S,5R,6R)-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylsulfinyl)heptan-1-ol

(2S,3S,4S,5R,6S)-7-hydroxy-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptyl p-toluenesulfonate

(2S,4R,5R)-1-(benzyloxy)-5-hydroxy-2,4,6-trimethylhept-6-en-3-one

(2S,3S,4R,5R,6S)-7-(benzyloxy)-2,4,6-trimethyl-1,3,5-heptanetriol

Downstream raw materials:

C₄₁H₆₉Cl₃O₉Si₂