Benzoic acid (2R,4R,6S)-2-allyl-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Benzoic acid (2R,4R,6S)-2-allyl-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester
CAS No.:476005-15-9
Molecular Formula:C₁₈H₂₄O₄
Molecular Weight:304.386
Hs Code.:

Synonyms:Benzoic acid (2R,4R,6S)-2-allyl-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Benzoic acid (2R,4R,6S)-2-allyl-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

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Technology Process of Benzoic acid (2R,4R,6S)-2-allyl-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

There total 5 articles about Benzoic acid (2R,4R,6S)-2-allyl-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-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: 91.0%

: 762-72-1
allyl-trimethyl-silane

: 476005-14-8
C₂₈H₃₈O₆Si

: 476005-15-9
Benzoic acid (2R,4R,6S)-2-allyl-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

: 476005-18-2
Benzoic acid (2R,4R,6S)-2-allyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 24h;
DOI:10.1016/S0040-4020(02)00635-X

Reference yield:

: 1027893-21-5
2-bromo-2-methyl-propionic acid 1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-propyl ester

: 476005-15-9
Benzoic acid (2R,4R,6S)-2-allyl-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 521.7 mg / samarium diiodide / tetrahydrofuran / 0.17 h / 0 °C

2: 322.4 mg / DIBAH / CH₂Cl₂; hexane / 0.08 h / -78 °C

3: 532.6 mg / pyridine / 11 h / 20 °C

4: 91 percent / BF₃*Et₂O; TMSOTf / acetonitrile / 24 h / 20 °C

With pyridine; samarium diiodide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 1: Reformatsky reaction;
DOI:10.1016/S0040-4020(02)00635-X

Reference yield:

: (4R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3,3-dimethyl-tetrahydro-pyran-2,4-diol

: 476005-15-9
Benzoic acid (2R,4R,6S)-2-allyl-6-hydroxymethyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 532.6 mg / pyridine / 11 h / 20 °C

2: 91 percent / BF₃*Et₂O; TMSOTf / acetonitrile / 24 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In acetonitrile;
DOI:10.1016/S0040-4020(02)00635-X