(2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol

Base Information

Chemical Name:(2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol
CAS No.:142929-77-9
Molecular Formula:C₁₆H₂₄O₃
Molecular Weight:264.365
Hs Code.:

Synonyms:(2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol

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Chemical Property of (2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol

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Technology Process of (2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol

There total 11 articles about (2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol 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%

: 73814-98-9,73814-99-0,105560-79-0,143005-16-7
(2R,3S)-5-Benzyloxy-2-methyl-pentane-1,3-diol

: 77-76-9
2,2-dimethoxy-propane

: 142929-77-9
(2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol

Guidance literature:: With toluene-4-sulfonic acid; for 36h;
DOI:10.1021/ol048574m

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 142929-77-9
(2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH, 2.) n-BuLi

2: 76 percent / <((S)-BINAP)RuCl₂>2*Et₃N, 2 N aq. HCl, H₂ / methanol / 24 h / 45 °C / 83777.9 Torr

3: 1.) LDA / 1.) THF, -40 deg C, 1.5 h, 2.) THF, N,N'-dimethylpropyleneurea (DMPU), a) -40 deg C, 30 min, b) 25 deg C, 17 h

4: LAH / diethyl ether / 0.5 h / 22 °C

5: camphorsulfonic acid (CSA) / acetone / 0.33 h

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; [(S)Ru(BINAP)Cl₂]2*NEt₃; camphor-10-sulfonic acid; hydrogen; sodium hydride; lithium diisopropyl amide; In methanol; diethyl ether; acetone;
DOI:10.1021/ja00084a017

Reference yield:

: 155391-85-8
1,1-dimethylethyl (3S)-3-hydroxy-5-(phenylmethoxy)pentanoate

: 142929-77-9
(2R,3S)-2-methyl-1,3-O-(1-methylethylidene)-5-O-(phenylmethyl)-1,3,5-pentanetriol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, -40 deg C, 1.5 h, 2.) THF, N,N'-dimethylpropyleneurea (DMPU), a) -40 deg C, 30 min, b) 25 deg C, 17 h

2: LAH / diethyl ether / 0.5 h / 22 °C

3: camphorsulfonic acid (CSA) / acetone / 0.33 h

With lithium aluminium tetrahydride; camphor-10-sulfonic acid; lithium diisopropyl amide; In diethyl ether; acetone;
DOI:10.1021/ja00084a017