1-Piperidinecarboxylic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-hydroxy-, phenylmethyl ester, (3R,5R)-

Base Information

• Chemical Name: 1-Piperidinecarboxylic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-hydroxy-, phenylmethyl ester, (3R,5R)-
• CAS No.: 497181-37-0
• Molecular Formula: C25H45NO5Si2
• Molecular Weight: 495.807
• Mol file: 497181-37-0.mol

Synonyms:

Chemical Property of 1-Piperidinecarboxylic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-hydroxy-, phenylmethyl ester, (3R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Piperidinecarboxylic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-hydroxy-, phenylmethyl ester, (3R,5R)-

There total 19 articles about 1-Piperidinecarboxylic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-hydroxy-, phenylmethyl ester, (3R,5R)- 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: 87.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3R,5R)-3,4,5-Trihydroxy-piperidine-1-carboxylic acid benzyl ester (497181-36-9) → (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)piperidin-4-ol (497181-37-0)

Guidance literature:

With triethylamine; 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)piperidin-4-ol (497181-37-0)

Guidance literature:

Multi-step reaction with 4 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

With hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; palladium dihydroxide; In methanol; diethyl ether; N,N-dimethyl-formamide;

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

Reference yield:

D-Mannose (530-26-7) → (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)piperidin-4-ol (497181-37-0)

Guidance literature:

Multi-step reaction with 11 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

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

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

upstream raw materials:

tert-butyldimethylsilyl chloride

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

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)-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

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

(3S,5S)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)piperidine