(3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Base Information

Chemical Name:(3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid
CAS No.:196102-90-6
Molecular Formula:C₄₂H₆₇N₃O₇Si
Molecular Weight:754.095
Hs Code.:

(3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Synonyms:(3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

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Chemical Property of (3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

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Technology Process of (3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

There total 13 articles about (3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic 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: 100.0%

: 196102-88-2
{(R)-1-[(S)-1-((S)-1-{[(1S,2R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyl]-methyl-carbamoyl}-2-methyl-propylcarbamoyl)-ethyl]-octyl}-carbamic acid benzyl ester

: 196102-90-6
(3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 25 ℃; for 15h;
DOI:10.1021/jo9708396

Reference yield:

: 13734-41-3
t-Boc-L-valine

: 196102-90-6
(3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / DIPEA, BOP / acetonitrile / 15 h / 25 °C

2: 98 percent / TFA / CH₂Cl₂ / 2 h / 25 °C

3: DIPEA, BOP / acetonitrile / 15 h / 25 °C

4: 87 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5: 92 percent / O₃, PPh₃ / CH₂Cl₂ / 1.) -78 deg C, 3 min, 2.) 25 deg C, 12 h

6: 100 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 15 h / 25 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo9708396

Reference yield:

: 124-13-0
Octanal

: 196102-90-6
(3R,4S)-4-{[(S)-2-((2S,3R)-3-Benzyloxycarbonylamino-2-methyl-decanoylamino)-3-methyl-butyryl]-methyl-amino}-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) t-BuOK, BuLi, 2.) (+)-B-methoxydiiosopinocampheylborane, 3.) BF₃*Et₂O, 5.) 3 M NaOH, 30percent H₂O₂ / 1.) THF, pentane, -78 deg C, 30 min, 2.) -78 deg C, 30 min, 4.) THF, -78 deg C, 2.5 h; 1.5 h, 5.) H₂O, 25 deg C, overnight

2: 95 percent / PPh₃, DIAD, DPPA / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) 25 deg C, 15 h

3: 1.) PPh₃, H₂O, 2.) DIPEA / 1.) THF, 25 deg C, 30 h, 2.) 25 deg C, 6 h

4: 90 percent / O₃, PPh₃ / CH₂Cl₂ / 1.) -78 deg C, 4 min, 2.) 25 deg C, 12 h

5: 100 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 15 h / 25 °C

6: DIPEA, BOP / acetonitrile / 15 h / 25 °C

7: 87 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8: 92 percent / O₃, PPh₃ / CH₂Cl₂ / 1.) -78 deg C, 3 min, 2.) 25 deg C, 12 h

9: 100 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 15 h / 25 °C

With 2,6-dimethylpyridine; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; diphenyl-phosphinic acid; potassium tert-butylate; water; dihydrogen peroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo9708396