(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one

Base Information

Chemical Name:(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one
CAS No.:835929-47-0
Molecular Formula:C₂₄H₃₈O₅Si
Molecular Weight:434.648
Hs Code.:

Synonyms:(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one

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Chemical Property of (5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one

There total 5 articles about (5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one 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:

: 916659-56-8
(S)-3-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)butanal

: 835929-47-0
(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi; t-BuOK / tetrahydrofuran; hexane / 0.33 h / -45 °C

1.2: (+)-β-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / 0.58 h / -78 °C

1.3: 1.21 g / BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

2.1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / -78 °C

3.1: 75 percent / (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh / CH₂Cl₂ / Heating

With dmap; n-butyllithium; potassium tert-butylate; triethylamine; (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol047686a

Reference yield:

: 835929-53-8
(S)-tert-butyl({1-[(4-methoxybenzyl)oxy]pent-4-en-2-yl}oxy)dimethylsilane

: 835929-47-0
(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: O₃ / diethyl ether / 0.33 h / -78 °C

1.2: PPh₃ / CH₂Cl₂ / 1 h / -78 °C

2.1: n-BuLi; t-BuOK / tetrahydrofuran; hexane / 0.33 h / -45 °C

2.2: (+)-β-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / 0.58 h / -78 °C

2.3: 1.21 g / BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

3.1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / -78 °C

4.1: 75 percent / (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh / CH₂Cl₂ / Heating

With dmap; n-butyllithium; potassium tert-butylate; ozone; triethylamine; (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ol047686a

Reference yield:

: 835929-46-9
(3R,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-3-methyl-hept-1-en-4-ol

: 835929-47-0
(5R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-propyl]-3,5-dimethyl-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / -78 °C

2: 75 percent / (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh / CH₂Cl₂ / Heating

With dmap; triethylamine; (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh; In dichloromethane;
DOI:10.1021/ol047686a