Benzoic acid (2R,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl ester
CAS No.:128694-47-3
Molecular Formula:C₁₅H₁₈O₅
Molecular Weight:278.305
Hs Code.:

Synonyms:Benzoic acid (2R,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2R,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl ester

There total 7 articles about Benzoic acid (2R,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl 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: 9.0%

: 128694-45-1
Benzoic acid (R)-4-hydroxy-1-((E)-2-methoxycarbonyl-vinyl)-butyl ester

: 128694-47-3
Benzoic acid (2R,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl ester

: 128694-46-2
Benzoic acid (2S,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at -78 ℃; for 4h;
DOI:10.1021/jo9619241

Reference yield:

: 66084-36-4
(E)-(R)-(tetrahydro-pyran-2-yloxy)-hex-2-en-1-ol

: 128694-47-3
Benzoic acid (2R,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

2: 80 percent / Ti(OPr-i)4 / CH₂Cl₂ / 4 h / Ambient temperature

3: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

4: 80 percent / NaH / benzene / 0.08 h / 0 °C

5: 95 percent / conc. HCl / methanol / 0.08 h / pH 1

6: 9 percent / NaH / tetrahydrofuran / 4 h / -78 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; diethyl (2R,3R)-tartrate; sodium hydride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; benzene;
DOI:10.1021/jo9619241

Reference yield:

: 127089-43-4
(E)-methyl-6-[(tetrahydro-2H-pyran-2-yl)oxy]-hex-2-en-oate

: 128694-47-3
Benzoic acid (2R,3R)-2-methoxycarbonylmethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / DIBAL / diethyl ether; hexane / 0.5 h / 0 °C

2: 81 percent / Ti(OPr-i)4, (R,R)-(+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

3: 80 percent / Ti(OPr-i)4 / CH₂Cl₂ / 4 h / Ambient temperature

4: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

5: 80 percent / NaH / benzene / 0.08 h / 0 °C

6: 95 percent / conc. HCl / methanol / 0.08 h / pH 1

7: 9 percent / NaH / tetrahydrofuran / 4 h / -78 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; diethyl (2R,3R)-tartrate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; benzene;
DOI:10.1021/jo9619241