(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 109181-80-8
• Molecular Formula: C₂₂H₃₇NO₆SSi
• Molecular Weight: 471.69
• Mol file: 109181-80-8.mol

Synonyms:(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

Chemical Property of (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

There total 9 articles about (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester 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: 84.0%

t-butyldimethylsiyl triflate (69739-34-0) + (3S,4S)-3-Hydroxy-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester (109175-05-5) → (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester (109181-80-8)

Guidance literature:

With lutidine; In dichloromethane; at -20 ℃;

DOI:10.1016/S0040-4039(00)84714-0

Reference yield:

Methyl 4-C-<(Dimethylcarboxamido)methyl>-2,3,4-trideoxy-α-D-erythrohex-2-enopyranoside (64889-23-2) → (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester (109181-80-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 86 percent / pyridine / 2 h / 0 °C

2: 89 percent / NaN₃ / dimethylformamide / 8 h / 65 °C

3: 1.) H₂, 2.) lithium diisopropylamide / 1.) palladium black / 1.) ethanol, 2.) THF, -40 deg C

4: LiAlH₄ / tetrahydrofuran

5: aq. NaHCO₃ / diethyl ether

6: 1.) TiCl₄, 2.) DBU / 1.) CDCl₃, -20 deg C, 10 min

7: 1.) O₃, 2.) NaBH₄ / 1.) methanol, dichloromethane, -65 deg C, 20 min

8: 84 percent / pyridine / -10 °C

9: 84 percent / lutidine / CH₂Cl₂ / -20 °C

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; lutidine; hydrogen; titanium tetrachloride; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84714-0

Reference yield:

2-((2S,3S,6S)-6-Methoxy-2-triazirin-1-ylmethyl-3,6-dihydro-2H-pyran-3-yl)-N,N-dimethyl-acetamide → (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester (109181-80-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) H₂, 2.) lithium diisopropylamide / 1.) palladium black / 1.) ethanol, 2.) THF, -40 deg C

2: LiAlH₄ / tetrahydrofuran

3: aq. NaHCO₃ / diethyl ether

4: 1.) TiCl₄, 2.) DBU / 1.) CDCl₃, -20 deg C, 10 min

5: 1.) O₃, 2.) NaBH₄ / 1.) methanol, dichloromethane, -65 deg C, 20 min

6: 84 percent / pyridine / -10 °C

7: 84 percent / lutidine / CH₂Cl₂ / -20 °C

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; lutidine; hydrogen; titanium tetrachloride; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)84714-0

upstream raw materials:

t-butyldimethylsiyl triflate

(3S,4S)-3-Hydroxy-4-(2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

Methyl 4-C-<(Dimethylcarboxamido)methyl>-2,3,4-trideoxy-α-D-erythrohex-2-enopyranoside

(3S,4S)-3-Hydroxy-4-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid benzyl ester

Downstream raw materials:

(S)-3-quinuclidinol