(2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-3-hydroxy-2,4-dimethyl-octadecanoic acid pentafluorophenyl ester

Base Information

Chemical Name:(2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-3-hydroxy-2,4-dimethyl-octadecanoic acid pentafluorophenyl ester
CAS No.:350817-29-7
Molecular Formula:C₅₀H₇₄F₅N₃O₁₁
Molecular Weight:988.143
Hs Code.:

(2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-3-hydroxy-2,4-dimethyl-octadecanoic acid pentafluorophenyl ester

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Chemical Property of (2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-3-hydroxy-2,4-dimethyl-octadecanoic acid pentafluorophenyl ester

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Technology Process of (2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-3-hydroxy-2,4-dimethyl-octadecanoic acid pentafluorophenyl ester

There total 5 articles about (2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-3-hydroxy-2,4-dimethyl-octadecanoic acid pentafluorophenyl 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: 66.0%

: 771-61-9
2,3,4,5,6-pentafluorophenol

: 350817-28-6
N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R)-1-[(1R,2R,3R)-3-carboxy-2-hydroxy-1-methylbutyl]tetradecyl ester

: 350817-29-7
(2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-3-hydroxy-2,4-dimethyl-octadecanoic acid pentafluorophenyl ester

Guidance literature:: With dicyclohexyl-carbodiimide;
DOI:10.1055/s-2001-13382

Reference yield:

: (S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid (R)-1-((S)-1-methyl-2-oxo-ethyl)-tetradecyl ester

: 350817-29-7
(2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-3-hydroxy-2,4-dimethyl-octadecanoic acid pentafluorophenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / -78 °C

2: 100 percent / DCC; HOBt

3: 87 percent / O₃; Ph₃P / -78 °C

4: 62 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O

5: 66 percent / DCC

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; benzotriazol-1-ol; ozone; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; water; tert-butyl alcohol; 1: Roush asymmetric alkylation;
DOI:10.1055/s-2001-13382

Reference yield:

: 350817-16-2
(S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid (R)-1-((1R,2S,3S)-2-hydroxy-1,3-dimethyl-pent-4-enyl)-tetradecyl ester

: 350817-29-7
(2R,3R,4R,5R)-5-{(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionyloxy}-3-hydroxy-2,4-dimethyl-octadecanoic acid pentafluorophenyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / DCC; HOBt

2: 87 percent / O₃; Ph₃P / -78 °C

3: 62 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O

4: 66 percent / DCC

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; benzotriazol-1-ol; ozone; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; water; tert-butyl alcohol;
DOI:10.1055/s-2001-13382