Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

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Chemical Name:Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester
CAS No.:153896-18-5
Molecular Formula:C₁₉H₂₆O₆
Molecular Weight:350.412
Hs Code.:

Synonyms:Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

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Chemical Property of Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

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Technology Process of Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

There total 9 articles about Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester 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: 84.0%

: 65-85-0,8013-63-6
benzoic acid

: 153896-17-4
{(2S,3S)-3-[(E)-4-(Tetrahydro-pyran-2-yloxy)-but-2-enyl]-oxiranyl}-methanol

: 153896-18-5
Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

Guidance literature:: With titanium(IV) isopropylate; In dichloromethane; Ambient temperature;
DOI:10.1016/S0040-4039(00)73936-0

Reference yield:

: 98234-53-8,119343-29-2
(E)-2-((4-bromobut-2-en-1-yl)oxy)tetrahydro-2H-pyran

: 153896-18-5
Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / copper(I) chloride / tetrahydrofuran / 12 h / Ambient temperature

2: 81 percent / LiAlH₄ / tetrahydrofuran / 4 h / -78 °C

3: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

4: 84 percent / Ti(OPr-i)4 / CH₂Cl₂ / 0.25 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; copper(l) chloride; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane;
DOI:10.1021/jo9619241

Reference yield:

: 77741-47-0
(E)-4-((tetrahydro-2H-pyran-2-yl)oxy)but-2-en-1-ol

: 153896-18-5
Benzoic acid (E)-(R)-1-((S)-1,2-dihydroxy-ethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

2: 88 percent / LiBr / dimethylformamide / 27 h / 0 °C

3: 75 percent / copper(I) chloride / tetrahydrofuran / 12 h / Ambient temperature

4: 81 percent / LiAlH₄ / tetrahydrofuran / 4 h / -78 °C

5: 80 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

6: 84 percent / Ti(OPr-i)4 / CH₂Cl₂ / 0.25 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; triethylamine; copper(l) chloride; lithium bromide; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo9619241