(1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

Base Information

Chemical Name:(1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate
CAS No.:403666-31-9
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

Synonyms:(1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

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Chemical Property of (1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

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Technology Process of (1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

There total 6 articles about (1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate 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: 99.0%

: 403666-30-8
(1'S,1R,2S,4R,5S)-(2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]octa-6-ene-3-one-4-yl) pivaloate

: 403666-31-9
(1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

Guidance literature:: (1'S,1R,2S,4R,5S)-(2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]octa-6-ene-3-one-4-yl) pivaloate; With cerium(III) chloride; In tetrahydrofuran; at 0 ℃; for 10h;

With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 11 ℃; for 3h;
DOI:10.1002/1521-3765(20011119)7:22<4771::AID-CHEM4771>3.0.CO;2-J

Reference yield:

: 3282-30-2
pivaloyl chloride

: 403666-31-9
(1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / DMAP; NEt₃ / CH₂Cl₂ / 1.67 h / 0 - 20 °C

2.1: 85 percent / DBU / acetonitrile / 1.67 h / 16 - 18 °C / Irradiation

3.1: aq. CeCl₃*5H₂O / tetrahydrofuran / 10 h / 0 °C

3.2: 99 percent / aq. NaBH₄ / tetrahydrofuran / 3 h / 0 - 11 °C

With dmap; cerium(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1002/1521-3765(20011119)7:22<4771::AID-CHEM4771>3.0.CO;2-J

Reference yield:

: 209852-87-9
(-)-(1'S,2S)-2α-(1-Phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-3-one

: 403666-31-9
(1'S,1R,2R,3S,4S,5S)-(3-hydroxy-2-(1'-phenylethoxy)-8-oxabicyclo[3.2.1]oct-6-en-4-yl) pivaloate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / LDA; NEt₃ / tetrahydrofuran; hexane / -78 °C

2.1: aq. mCPBA / tetrahydrofuran / 2.5 h / 0 - 20 °C

2.2: 78 percent / TFA / tetrahydrofuran; H₂O / 4 h / 20 °C

3.1: 95 percent / DMAP; NEt₃ / CH₂Cl₂ / 1.67 h / 0 - 20 °C

4.1: 85 percent / DBU / acetonitrile / 1.67 h / 16 - 18 °C / Irradiation

5.1: aq. CeCl₃*5H₂O / tetrahydrofuran / 10 h / 0 °C

5.2: 99 percent / aq. NaBH₄ / tetrahydrofuran / 3 h / 0 - 11 °C

With dmap; cerium(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1002/1521-3765(20011119)7:22<4771::AID-CHEM4771>3.0.CO;2-J