Acetic acid (1S,2S,4R)-1-((S)-2-acetoxy-1-methyl-ethyl)-5-benzyloxymethoxy-2,4-dimethyl-pentyl ester

Base Information

Chemical Name:Acetic acid (1S,2S,4R)-1-((S)-2-acetoxy-1-methyl-ethyl)-5-benzyloxymethoxy-2,4-dimethyl-pentyl ester
CAS No.:94339-73-8
Molecular Formula:C₂₂H₃₄O₆
Molecular Weight:394.508
Hs Code.:

Synonyms:

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Chemical Property of Acetic acid (1S,2S,4R)-1-((S)-2-acetoxy-1-methyl-ethyl)-5-benzyloxymethoxy-2,4-dimethyl-pentyl ester

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Technology Process of Acetic acid (1S,2S,4R)-1-((S)-2-acetoxy-1-methyl-ethyl)-5-benzyloxymethoxy-2,4-dimethyl-pentyl ester

There total 2 articles about Acetic acid (1S,2S,4R)-1-((S)-2-acetoxy-1-methyl-ethyl)-5-benzyloxymethoxy-2,4-dimethyl-pentyl 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: 89.0%

: 94339-72-7,94424-82-5
(2R,3R,4R,6S)-7-Benzyloxymethoxy-2,4,6-trimethyl-heptane-1,3-diol

: 94339-73-8,94424-83-6
Acetic acid (1S,2S,4R)-1-((S)-2-acetoxy-1-methyl-ethyl)-5-benzyloxymethoxy-2,4-dimethyl-pentyl ester

Guidance literature:: DOI:10.1016/S0040-4039(01)91187-6

Reference yield:

: 94339-71-6,94424-81-4
[(2S,3R)-3-((1R,3S)-4-Benzyloxymethoxy-1,3-dimethyl-butyl)-2-methyl-oxiranyl]-methanol

: 94339-73-8,94424-83-6
Acetic acid (1S,2S,4R)-1-((S)-2-acetoxy-1-methyl-ethyl)-5-benzyloxymethoxy-2,4-dimethyl-pentyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Red-al / tetrahydrofuran / 48 h / 45 °C

2: 89 percent

With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(01)91187-6

Reference yield:

: 94339-73-8,94424-83-6
Acetic acid (1S,2S,4R)-1-((S)-2-acetoxy-1-methyl-ethyl)-5-benzyloxymethoxy-2,4-dimethyl-pentyl ester

: 79495-87-7
protomycinolide IV

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) H₂, 2.)RuCl₃ / 1.) 5percent Pd-C / 1.) THF, 5 days, 2.) H₂O-CH₃CN-CCl₄

2: LiOH / H₂O; tetrahydrofuran

3: Swern oxidation

4: 41 percent / NaH / tetrahydrofuran

5: KOH / H₂O; methanol

6: imidazole / dimethylformamide / 50 °C

7: KF*2H₂O / dimethylformamide / 0.5 h / Ambient temperature

8: (COCl)2 / benzene

9: diethyl ether / -100 °C

10: 1.)t-BuOK / 1.) THF, ether, -78 deg C then rt, 2.) rt then 80 deg C

11: 1.)PPTS, 2.)NaBH₄-CeCl₃ / 1.) MeOH, 50 deg C, 2.) MeOH, O deg C

12: 95 percent / KOH / methanol; H₂O / 50 °C

13: TCBA

14: Swern oxidation

15: HF / acetonitrile

With 1H-imidazole; ruthenium trichloride; potassium fluoride; potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; 2,3,6-TBA; hydrogen fluoride; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)91187-6