(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
Hs Code.:

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

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

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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%

: 89031-84-5
3-(tert-butyldimethylsilyloxy)propyl bromide

: 497181-37-0
(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)piperidin-4-ol

: 497181-39-2
(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)-4-[3'-(tert-butyldimethylsilyloxy)propoxy]piperidine

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

: 497181-39-2
(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)-4-[3'-(tert-butyldimethylsilyloxy)propoxy]piperidine

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:

: 530-26-7
D-Mannose

: 497181-39-2
(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)-4-[3'-(tert-butyldimethylsilyloxy)propoxy]piperidine

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