(3R,5S)-methyl 3,5-O-benzylidene-6-hexadecenoate

Base Information

Chemical Name:(3R,5S)-methyl 3,5-O-benzylidene-6-hexadecenoate
CAS No.:310904-17-7
Molecular Formula:C₂₄H₃₆O₄
Molecular Weight:388.547
Hs Code.:

Synonyms:(3R,5S)-methyl 3,5-O-benzylidene-6-hexadecenoate

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Chemical Property of (3R,5S)-methyl 3,5-O-benzylidene-6-hexadecenoate

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Technology Process of (3R,5S)-methyl 3,5-O-benzylidene-6-hexadecenoate

There total 9 articles about (3R,5S)-methyl 3,5-O-benzylidene-6-hexadecenoate 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: 56.0%

: 32339-43-8
decyltriphenylphosphonium bromide

: 310904-16-6
(3R,5S)-methyl 3,5-O-benzylidene-6-oxohexanoate

: 310904-17-7
(3R,5S)-methyl 3,5-O-benzylidene-6-hexadecenoate

Guidance literature:: decyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

(3R,5S)-methyl 3,5-O-benzylidene-6-oxohexanoate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2.5h;
DOI:10.1248/cpb.48.1545

Reference yield:

: 74091-54-6
3-Phenyl-2,4,10-trioxa-adamantane

: 310904-17-7
(3R,5S)-methyl 3,5-O-benzylidene-6-hexadecenoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 70 percent / BH₃*THF / tetrahydrofuran; hexamethylphosphoric acid triamide / 60 h / -15 °C

2.1: 70 percent / triacetoxy periodinane / CH₂Cl₂ / 0.25 h / 0 °C

3.1: 75 percent / lithium (S,S)-α,α'-dimethylbenzylamide / tetrahydrofuran; hexane / 0.17 h / -100 °C

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: 85 percent / PPh₃ / CH₂Cl₂ / 1 h / -78 - 20 °C

5.1: 93 percent / NaBH₄ / methanol / 3 h / 20 °C

6.1: 100 percent / K₂CO₃ / dimethylformamide / 0.17 h / 20 °C

7.1: 100 percent / (COCl)2; DMSO / CH₂Cl₂ / -78 - 0 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.2: 56 percent / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

With sodium tetrahydroborate; n-butyllithium; borane-THF; oxalyl dichloride; potassium carbonate; Dess-Martin periodane; lithium (S,S)-bis(α-methylbenzyl)amide; ozone; dimethyl sulfoxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide; 8.2: Wittig olefination;
DOI:10.1248/cpb.48.1545

Reference yield:

: 707-07-3
orthobenzoic acid trimethyl ester

: 310904-17-7
(3R,5S)-methyl 3,5-O-benzylidene-6-hexadecenoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 20 °C

2.1: 70 percent / BH₃*THF / tetrahydrofuran; hexamethylphosphoric acid triamide / 60 h / -15 °C

3.1: 70 percent / triacetoxy periodinane / CH₂Cl₂ / 0.25 h / 0 °C

4.1: 75 percent / lithium (S,S)-α,α'-dimethylbenzylamide / tetrahydrofuran; hexane / 0.17 h / -100 °C

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: 85 percent / PPh₃ / CH₂Cl₂ / 1 h / -78 - 20 °C

6.1: 93 percent / NaBH₄ / methanol / 3 h / 20 °C

7.1: 100 percent / K₂CO₃ / dimethylformamide / 0.17 h / 20 °C

8.1: 100 percent / (COCl)2; DMSO / CH₂Cl₂ / -78 - 0 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.2: 56 percent / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

With sodium tetrahydroborate; n-butyllithium; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; potassium carbonate; Dess-Martin periodane; lithium (S,S)-bis(α-methylbenzyl)amide; ozone; dimethyl sulfoxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide; 9.2: Wittig olefination;
DOI:10.1248/cpb.48.1545