(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(S)-4-tert-butoxycarbonylamino-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyl]-piperidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(S)-4-tert-butoxycarbonylamino-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyl]-piperidine-1-carboxylic acid benzyl ester
CAS No.:860264-66-0
Molecular Formula:C₆₂H₇₁N₃O₁₁
Molecular Weight:1034.26
Hs Code.:

(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(S)-4-tert-butoxycarbonylamino-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyl]-piperidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(S)-4-tert-butoxycarbonylamino-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyl]-piperidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(S)-4-tert-butoxycarbonylamino-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyl]-piperidine-1-carboxylic acid benzyl ester

There total 9 articles about (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(S)-4-tert-butoxycarbonylamino-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyl]-piperidine-1-carboxylic acid benzyl 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:

: (2S,3S,4R,5S,6S)-2-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-piperidine

: 860264-66-0
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(S)-4-tert-butoxycarbonylamino-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyl]-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: NaHCO₃ / ethanol; H₂O / 1 h / 0 °C

2: 50 percent / Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C

3: 82 percent / toluene-p-sulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 85 °C

4: Jones reagent / acetone / 3.5 h / 0 - 20 °C

5: 80 percent / PyBOP; DIPEA / CH₂Cl₂ / 2 h / 20 °C

With jones reagent; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium acetate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetone;
DOI:10.1021/jo050494o

Reference yield:

: 860264-34-2
(2S,3S,4R,5S,6S)-N-benzyloxycarbonyl-6-benzyloxymethyl-3,4,5-tribenzyloxy-2-(2-propenyl)piperidine

: 860264-66-0
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(S)-4-tert-butoxycarbonylamino-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyl]-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 50 percent / Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C

2: 82 percent / toluene-p-sulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 85 °C

3: Jones reagent / acetone / 3.5 h / 0 - 20 °C

4: 80 percent / PyBOP; DIPEA / CH₂Cl₂ / 2 h / 20 °C

With jones reagent; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium acetate; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In 1,2-dimethoxyethane; dichloromethane; acetone;
DOI:10.1021/jo050494o

Reference yield:

: 133625-87-3
tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate

: 860264-66-0
(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(S)-4-tert-butoxycarbonylamino-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyl]-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 50 percent / Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C

2: 82 percent / toluene-p-sulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 85 °C

3: Jones reagent / acetone / 3.5 h / 0 - 20 °C

4: 80 percent / PyBOP; DIPEA / CH₂Cl₂ / 2 h / 20 °C

With jones reagent; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium acetate; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In 1,2-dimethoxyethane; dichloromethane; acetone;
DOI:10.1021/jo050494o