(2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

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Chemical Name:(2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate
CAS No.:1613724-80-3
Molecular Formula:C₃₅H₆₁NO₇
Molecular Weight:607.872
Hs Code.:

Synonyms:(2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

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Chemical Property of (2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

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Technology Process of (2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

There total 13 articles about (2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate 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: 76.0%

: 1613724-79-0
(2S,3R)-2-[(4S,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]hexadecan-3-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

: 1613724-80-3
(2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

Guidance literature:: With acetic acid; In water; at 20 ℃; for 10h; Inert atmosphere;
DOI:10.1002/hlca.201300255

Reference yield:

: 23680-31-1
BOC-O-benzyl-L-serine

: 1613724-80-3
(2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

1.2: 2.5 h / 0 °C / Inert atmosphere

2.1: acetic acid / water / 10 h / 20 °C / Inert atmosphere

With dmap; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; water;
DOI:10.1002/hlca.201300255

Reference yield:

: 112-72-1
1-Tetradecanol

: 1613724-80-3
(2S,3S,4R,5R)-1,3-dihydroxy-2,4-dimethyloctadecan-5-yl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

1.2: -78 - -50 °C / Inert atmosphere

2.1: benzene / Reflux; Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -10 °C / Inert atmosphere

4.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate; tert.-butylhydroperoxide / dichloromethane; toluene / 2.83 h / -25 °C / Molecular sieve; Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / -45 °C / Molecular sieve; Inert atmosphere

6.1: hydrogenchloride / water; tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

7.1: benzene / 12 h / Reflux; Inert atmosphere

8.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -10 °C / Inert atmosphere

9.1: dimethylsulfide borane complex / tetrahydrofuran / 4.25 h / -10 - 0 °C / Inert atmosphere

10.1: (1S)-10-camphorsulfonic acid / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

11.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

11.2: 2.5 h / 0 °C / Inert atmosphere

12.1: acetic acid / water / 10 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; oxalyl dichloride; diethyl (2S,3S)-tartrate; dimethylsulfide borane complex; (1S)-10-camphorsulfonic acid; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; toluene; benzene; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 2.1: |Wittig Olefination / 4.1: |Sharpless Asymmetric Epoxidation / 7.1: |Wittig Olefination;
DOI:10.1002/hlca.201300255