(2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid

Base Information

Chemical Name:(2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid
CAS No.:1028272-13-0
Molecular Formula:C₂₁H₃₄O₆
Molecular Weight:382.497
Hs Code.:

Synonyms:(2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid

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Chemical Property of (2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid

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Technology Process of (2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid

There total 11 articles about (2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid 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:

: 160531-40-8
(S)-3-((2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoyl)-4-isopropyl-oxazolidin-2-one

: 1028272-13-0
(2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 1.5h;
DOI:10.1021/jo00096a003

Reference yield:

: 16451-50-6
(S)-4-methyl-pentane-1,3-diol

: 1028272-13-0
(2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N, DMAP / CH₂Cl₂ / 13 h / 20 °C

2: NaH / dimethylformamide / 2.5 h / Ambient temperature

3: conc. HCl / methanol; tetrahydrofuran / 4 h / 30 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) -78 deg C to 0 deg C, 15 min

5: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

6: Me₃Al / tetrahydrofuran / 2 h / -19 - -6 °C

7: i-Pr₂NEt / 2 h

8: DIBAL / tetrahydrofuran / 0.17 h / -78 °C

9: Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

10: aq. LiOH, H₂O₂ / tetrahydrofuran / 1.5 h / 0 °C

With hydrogenchloride; dmap; lithium hydroxide; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00096a003

Reference yield:

: 100-39-0
benzyl bromide

: 1028272-13-0
(2S,3R,4R,5R,7S)-7-Benzyloxy-3-hydroxy-5-methoxymethoxy-2,4,8-trimethyl-nonanoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: NaH / dimethylformamide / 2.5 h / Ambient temperature

2: conc. HCl / methanol; tetrahydrofuran / 4 h / 30 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) -78 deg C to 0 deg C, 15 min

4: 95 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

5: Me₃Al / tetrahydrofuran / 2 h / -19 - -6 °C

6: i-Pr₂NEt / 2 h

7: DIBAL / tetrahydrofuran / 0.17 h / -78 °C

8: Bu₂BOTf, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) -78 deg C to 0 deg C, 1 h

9: aq. LiOH, H₂O₂ / tetrahydrofuran / 1.5 h / 0 °C

With hydrogenchloride; lithium hydroxide; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00096a003