(R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: (R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester
• CAS No.: 226254-77-9
• Molecular Formula: C₂₀H₂₉NO₄Si
• Molecular Weight: 375.54
• Mol file: 226254-77-9.mol

Synonyms:(R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester

Chemical Property of (R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester

There total 5 articles about (R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic 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: 26.0%

(furan-2-yl)ethylene (1487-18-9) + O-benzyl carbamate (621-84-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester (226254-77-9) + (1R)-(2-furan-2-yl-2-hydroxy-ethyl)-carbamic acid benzyl ester (226254-73-5) + (1S)-(2-furan-2-yl-2-hydroxy-ethyl)-carbamic acid benzyl ester

Guidance literature:

(furan-2-yl)ethylene; O-benzyl carbamate; With sodium hydroxide; Hydroquinone 1,4-phthalazinediyl diether; tert-butylhypochlorite; osmium(VIII) oxide; In diethyl ether; water; tert-butyl alcohol; at 25 ℃; for 1h;

tert-butyldimethylsilyl chloride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ol016743m

Reference yield:

(furan-2-yl)ethylene (1487-18-9) + sodium [(benzyloxy)carbonyl]chloroamide (91174-01-5) + tert-butyldimethylsilyl chloride (18162-48-6) → benzyl N-{(1S)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-(furan-2-yl)ethyl}carbamate + (R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester (226254-77-9)

Guidance literature:

(furan-2-yl)ethylene; sodium [(benzyloxy)carbonyl]chloroamide; With osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In diethyl ether;

tert-butyldimethylsilyl chloride; Title compound not separated from byproducts;

DOI:10.1021/ol006907j

Reference yield:

furfural (98-01-1) → (R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester (226254-77-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Mg / diethyl ether / 1 h / Heating

1.2: 90 percent / diethyl ether / 12 h

2.1: aq. HCl / diethyl ether / 1 h

3.1: OsO₄; (DHQ)2PHAL / diethyl ether; 2-methyl-propan-2-ol; H₂O / 1 h / 25 °C

3.2: 3.71 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 23 °C

With hydrogenchloride; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; magnesium; In diethyl ether; water; tert-butyl alcohol; 1.2: Grignard reaction;

DOI:10.1021/ol006907j

upstream raw materials:

(furan-2-yl)ethylene

sodium [(benzyloxy)carbonyl]chloroamide

tert-butyldimethylsilyl chloride

O-benzyl carbamate

Downstream raw materials:

(2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

(2R,3R,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3,4,5-trihydroxy-piperidine-1-carboxylic acid benzyl ester

(2R,3S,4R,5R)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3,4,5-trihydroxypiperidine-1-carboxylic acid benzyl ester

(2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester