(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

Base Information

• Chemical Name: (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
• CAS No.: 860295-58-5
• Molecular Formula: C₃₃H₅₄O₅Si
• Molecular Weight: 558.874
• Mol file: 860295-58-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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: 80.0%

Acetic acid (2R,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl ester (860295-52-9) + (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 (860295-53-0) → (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 (860295-58-5)

Guidance literature:

Acetic acid (2R,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl ester; With n-butyllithium; In hexane; dichloromethane; at -30 ℃; for 0.5h;

With dimethylaluminum triflate; In hexane; dichloromethane; at -30 ℃; for 0.5h;

(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; In hexane; dichloromethane; at -30 - 20 ℃; for 1h;

DOI:10.1021/ol050864v

Reference yield:

(2S,4R,6S)-4-Methoxy-6-methyl-tetrahydro-pyran-2-ol → (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 (860295-58-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3.11 g / DMAP; pyridine / CH₂Cl₂; toluene / 1 h / 20 °C

2.1: nBuLi / CH₂Cl₂; hexane / 0.5 h / -30 °C

2.2: Me₂AlOTf / CH₂Cl₂; hexane / 0.5 h / -30 °C

2.3: 80 percent / CH₂Cl₂; hexane / 1 h / -30 - 20 °C

With pyridine; dmap; n-butyllithium; In hexane; dichloromethane; toluene;

DOI:10.1021/ol050864v

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) → (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 (860295-58-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 74 percent / 2,6-lutidine / CH₂Cl₂ / 66 h / 30 °C

2.1: 92 percent / DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

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

4.1: 1.15 g / Ph₃P; pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 90 percent / nBuLi / tetrahydrofuran; hexane / 0.5 h / -30 °C

6.1: nBuLi / CH₂Cl₂; hexane / 0.5 h / -30 °C

6.2: Me₂AlOTf / CH₂Cl₂; hexane / 0.5 h / -30 °C

6.3: 80 percent / CH₂Cl₂; hexane / 1 h / -30 - 20 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; 3.1: Swern oxidation / 4.1: Wittig reaction;

DOI:10.1021/ol050864v

upstream raw materials:

Acetic acid (2R,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl ester

(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

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

(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