(3R,4S,5R)-1-benzyloxycarbonyl-4,5-isopropylidenedioxypiperidin-3-ol

Base Information

• Chemical Name: (3R,4S,5R)-1-benzyloxycarbonyl-4,5-isopropylidenedioxypiperidin-3-ol
• CAS No.: 497181-35-8
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.346
• Mol file: 497181-35-8.mol

Synonyms:(3R,4S,5R)-1-benzyloxycarbonyl-4,5-isopropylidenedioxypiperidin-3-ol

Chemical Property of (3R,4S,5R)-1-benzyloxycarbonyl-4,5-isopropylidenedioxypiperidin-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-1-benzyloxycarbonyl-4,5-isopropylidenedioxypiperidin-3-ol

There total 17 articles about (3R,4S,5R)-1-benzyloxycarbonyl-4,5-isopropylidenedioxypiperidin-3-ol 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:

5-azido-5-deoxy-2,3-O-isopropylidene-α/β-D-lyxofuranose → (3R,4S,5R)-1-benzyloxycarbonyl-4,5-isopropylidenedioxypiperidin-3-ol (497181-35-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd(OH)2 / methanol / 14 h / 20 °C / 760 Torr

2: aq. NaHCO₃ / diethyl ether / 21 h / 20 °C

With hydrogen; sodium hydrogencarbonate; palladium dihydroxide; In methanol; diethyl ether;

DOI:10.3987/com-03-s(p)34

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + (3aR,7R,7aS)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-ol (170554-25-3) → (3R,4S,5R)-1-benzyloxycarbonyl-4,5-isopropylidenedioxypiperidin-3-ol (497181-35-8)

Guidance literature:

With sodium hydrogencarbonate; In diethyl ether;

DOI:10.1016/S0960-894X(02)00800-4

Reference yield:

D-Mannose (530-26-7) → (3R,4S,5R)-1-benzyloxycarbonyl-4,5-isopropylidenedioxypiperidin-3-ol (497181-35-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: CuSO₄; H₂SO₄

1.2: 86 percent / pyridine

2.1: 100 percent / 70 percent aq. AcOH

3.1: aq. NaIO₄ / diethyl ether

4.1: NaBH₄ / methanol

5.1: 75 percent / pyridine

6.1: 72 percent / NaN₃ / dimethylformamide

7.1: 97 percent / aq. NaOH / methanol

8.1: H₂ / Pd(OH)2 / methanol

9.1: aq. NaHCO₃ / diethyl ether

With pyridine; sodium hydroxide; sodium tetrahydroborate; sodium periodate; sodium azide; sulfuric acid; hydrogen; sodium hydrogencarbonate; copper(II) sulfate; acetic acid; palladium dihydroxide; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(02)00800-4

upstream raw materials:

benzyl chloroformate

(3aR,7R,7aS)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-ol

1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside

(+)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranos-3-yl benzoate

Downstream raw materials:

(3R,5R)-3,4,5-Trihydroxy-piperidine-1-carboxylic acid benzyl ester

(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine

(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)-4-[3'-(tert-butyldimethylsilyloxy)propoxy]piperidine

(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-phenoxythiocarbonyloxy-piperidine-1-carboxylic acid benzyl ester