(2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol

Base Information

• Chemical Name: (2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol
• CAS No.: 191530-29-7
• Molecular Formula: C₂₂H₃₂N₂O₇
• Molecular Weight: 436.505
• Mol file: 191530-29-7.mol

Synonyms:(2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol

Chemical Property of (2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol

There total 1 articles about (2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol 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: 86.0%

benzyl chloroformate (501-53-1,94274-21-2) + (2S,3R,4S,5R)-2-amino-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-O-isopropylidene-3,4-piperidinediol (176640-82-7) → (2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol (191530-29-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In methanol; at 0 ℃; for 1.5h;

DOI:10.1021/jm960627l

Reference yield: 80.0%

(2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol (191530-29-7) → (3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid (191530-30-0)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In tetrachloromethane; acetonitrile; for 0.666667h; Ambient temperature;

DOI:10.1021/jm960627l

Reference yield:

(2S,3R,4S,5R)-2-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidenepiperidine-3,4-diol (191530-29-7) → C35H49N5O9 (191530-55-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / aq. NaIO₄, RuO₂ / CCl₄; acetonitrile / 0.67 h / Ambient temperature

2: 94 percent / CH₂Cl₂; methanol / Ambient temperature

3: 70 percent / t-BuOK / tetrahydrofuran / 2 h / 0 °C

4: 70 percent / DBU / CH₂Cl₂ / 0.08 h / Ambient temperature

5: 95 percent / aq. p-toluenesulfonic acid, pyridine / 2 h / 80 °C

6: 68 percent / NaBH₄ / ethanol / 0.83 h / Ambient temperature

7: 98 percent / HgCl₂, Et₃N / dimethylformamide / 1 h / 0 °C

8: H₂ / 10percent Pd/C / acetonitrile / 0.5 h / Ambient temperature

With pyridine; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; mercury dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm960627l

upstream raw materials:

benzyl chloroformate

(2S,3R,4S,5R)-2-amino-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-O-isopropylidene-3,4-piperidinediol

Downstream raw materials:

(3S,4S,5R,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4,5-dihydroxy-4,5-O-isopropylidenepiperidine-3-carboxylic acid

(3R,4S,5S,6S)-6-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-5-hydroxy-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

(5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-3,4-didehydro-3-[(diphenylmethoxy)carbonyl]piperidine

(3R,4S,5S,6S)-4-amino-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine