(2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester
• CAS No.: 190320-46-8
• Molecular Formula: C₂₂H₃₄O₇SSi
• Molecular Weight: 470.659
• Mol file: 190320-46-8.mol

Synonyms:(2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester

Chemical Property of (2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester

There total 5 articles about (2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-ethyl]-3,6-dihydro-2H-pyran-2-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: 87.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,6S)-6-((R)-1-Hydroxy-2-methanesulfonyloxy-ethyl)-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester (216988-18-0) → (2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester (190320-46-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0040-4039(97)00422-X

Reference yield:

benzyl bromide (100-39-0) → (2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester (190320-46-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / DBU / acetonitrile / Ambient temperature

2: 93 percent / 4:1 AcOH:H₂O / Ambient temperature

3: 86 percent / collidine / CH₂Cl₂ / 0 °C

4: 87 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; 2,3,5-trimethyl-pyridine; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(97)00422-X

Reference yield:

(5S,6R)-5-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-6-vinyl-[1,4]dioxan-2-one → (2R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-ethyl]-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester (190320-46-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / LiHMDS, TMSCl, Et₃N / tetrahydrofuran / -78 °C

2: 80 percent / DBU / acetonitrile / Ambient temperature

3: 93 percent / 4:1 AcOH:H₂O / Ambient temperature

4: 86 percent / collidine / CH₂Cl₂ / 0 °C

5: 87 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; 2,3,5-trimethyl-pyridine; chloro-trimethyl-silane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(97)00422-X

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,6S)-6-((R)-1-Hydroxy-2-methanesulfonyloxy-ethyl)-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester

benzyl bromide

(2R,6S)-6-((R)-1,2-Dihydroxy-ethyl)-3,6-dihydro-2H-pyran-2-carboxylic acid benzyl ester