(2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran
• CAS No.: 924286-07-7
• Molecular Formula: C₂₆H₃₆O₃Si
• Molecular Weight: 424.656
• Mol file: 924286-07-7.mol

Synonyms:(2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran

Chemical Property of (2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran

There total 9 articles about (2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran 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:

(5S,6R)-6-[(1S)-2-(tert-butyl-diphenylsilanyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-pyran-2-one (924286-01-1) + methanol (67-56-1) → (2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran (924286-07-7)

Guidance literature:

(5S,6R)-6-[(1S)-2-(tert-butyl-diphenylsilanyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-pyran-2-one; With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h;

methanol; pyridinium p-toluenesulfonate; at 25 ℃; for 0.166667h;

DOI:10.1021/ja066477d

Reference yield:

(2S,3R,4S)-3-acryloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhex-5-ene (924286-00-0) → (2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran (924286-07-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / Grubbs' I catalyst / CH₂Cl₂ / 12 h / 40 °C

2.1: DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

2.2: PPTS / 0.17 h / 25 °C

With diisobutylaluminium hydride; Grubbs catalyst first generation; In dichloromethane; toluene;

DOI:10.1021/ja066477d

Reference yield:

(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol (95514-04-8) → (2R,5S,6S)-6-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethyl]-5-methyl-2-methoxy-5,6-dihydro-2H-pyran (924286-07-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 91 percent / iPr₂NEt / CH₂Cl₂ / 2 h / 25 °C

3.1: 89 percent / Grubbs' I catalyst / CH₂Cl₂ / 12 h / 40 °C

4.1: DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

4.2: PPTS / 0.17 h / 25 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In dichloromethane; toluene;

DOI:10.1021/ja066477d

upstream raw materials:

(5S,6R)-6-[(1S)-2-(tert-butyl-diphenylsilanyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-pyran-2-one

methanol

(2S,3R,4S)-3-acryloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhex-5-ene

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

Downstream raw materials:

bis[(9H-fluoren-9-yl)methyl](2S,3S,6S)-1-(4-methoxybenzyloxy)-2-methyl-6-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)heptan-3-yl phosphate

(2S,3S,6R)-2-[(2S,5S,6R)-5-triethylsilyloxy-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

(2S,3S,6R)-2-[(2S,5S,6S)-5-(1-ethoxyethyloxy)-7-(4-methoxybenzyloxy)-6-methylheptan-2-yl]-6-methoxy-3-methyl-3,6-dihydro-2H-pyran

6-[4-hydroxy-6-(4-methoxy-benzyloxy)-1,5-dimethyl-hexyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol