(E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic acid

Base Information

Chemical Name:(E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic acid
CAS No.:189246-49-9
Molecular Formula:C₂₈H₄₇NO₅
Molecular Weight:477.685
Hs Code.:

Synonyms:(E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic acid

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Chemical Property of (E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic acid

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Technology Process of (E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic acid

There total 13 articles about (E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic 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:

: 189246-47-7
(E)-(1R,2S,3S)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-((2S,5R)-3,6-diethoxy-2,5-dimethyl-2,5-dihydro-pyrazin-2-yl)-octadec-4-en-1-ol

: 189246-49-9
(E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / TBAF / tetrahydrofuran

2: 1.) aq. p-TsOH, 2.) 0.5 N aq. NaOH / 1.) EtOH, RT, 2.) MeOH

With sodium hydroxide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran;
DOI:10.1021/ja9730829

Reference yield:

: 181211-21-2
(E)-(2R,3S)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-octadec-4-enal

: 189246-49-9
(E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) BuLi, 2.) SnCl₂

2: 95 percent / TBAF / tetrahydrofuran

3: 1.) aq. p-TsOH, 2.) 0.5 N aq. NaOH / 1.) EtOH, RT, 2.) MeOH

With sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; tin(ll) chloride; In tetrahydrofuran;
DOI:10.1021/ja9730829

Reference yield:

: 765-09-3
1-bromotridecane

: 189246-49-9
(E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) BuLi, 2.) HMPA / 1.) THF, 2.) THF, from -78 deg C to RT

2: 96 percent / 3 N aq. HCl / tetrahydrofuran / Ambient temperature

3: Et₃N, DMAP / CH₂Cl₂ / 0 °C

4: LiAlH₄ / tetrahydrofuran / Heating

5: imidazole / dimethylformamide

6: 83 percent / HCOOH / diethyl ether

7: 95 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -50 °C

8: 1.) BuLi, 2.) SnCl₂

9: 95 percent / TBAF / tetrahydrofuran

10: 1.) aq. p-TsOH, 2.) 0.5 N aq. NaOH / 1.) EtOH, RT, 2.) MeOH

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; formic acid; oxalyl dichloride; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; tin(ll) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja9730829