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

Base Information

• Chemical Name: (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)-4-[3'-(tert-butyldimethylsilyloxy)propoxy]piperidine
• CAS No.: 497181-39-2
• Molecular Formula: C₃₄H₆₅NO₆Si₃
• Molecular Weight: 668.15
• Mol file: 497181-39-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)-4-[3'-(tert-butyldimethylsilyloxy)propoxy]piperidine 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: 20.0%

3-(tert-butyldimethylsilyloxy)propyl bromide (89031-84-5) + (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)piperidin-4-ol (497181-37-0) → (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)-4-[3'-(tert-butyldimethylsilyloxy)propoxy]piperidine (497181-39-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

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

Reference yield:

5-azido-5-deoxy-2,3-O-isopropylidene-α/β-D-lyxofuranose → (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)-4-[3'-(tert-butyldimethylsilyloxy)propoxy]piperidine (497181-39-2)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 92 percent / aq. AcOH / 18 h / 90 °C

4: 87 percent / Et₃N / dimethylformamide / 2 h / 20 °C

5: 20 percent / sodium hydride / dimethylformamide / 4 h / 20 °C

With hydrogen; sodium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; palladium dihydroxide; In methanol; diethyl ether; N,N-dimethyl-formamide; 5: Williamson ether synthesis;

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

Reference yield:

D-Mannose (530-26-7) → (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)-4-[3'-(tert-butyldimethylsilyloxy)propoxy]piperidine (497181-39-2)

Guidance literature:

Multi-step reaction with 12 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

10.1: 92 percent / 80 percent aq. AcOH / 90 °C

11.1: 87 percent / Et₃N / dimethylformamide

12.1: 20 percent / NaH / dimethylformamide

With pyridine; sodium hydroxide; sodium tetrahydroborate; sodium periodate; sodium azide; sulfuric acid; hydrogen; sodium hydride; sodium hydrogencarbonate; copper(II) sulfate; acetic acid; triethylamine; palladium dihydroxide; In methanol; diethyl ether; N,N-dimethyl-formamide; 12.1: Williamson synthesis;

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

upstream raw materials:

3-(tert-butyldimethylsilyloxy)propyl bromide

(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)piperidin-4-ol

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

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