(R)-4-Bromo-4-[(3aS,4R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-butyric acid ethyl ester

Base Information

• Chemical Name: (R)-4-Bromo-4-[(3aS,4R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-butyric acid ethyl ester
• CAS No.: 127391-18-8
• Molecular Formula: C₂₀H₂₈BrNO₆S
• Molecular Weight: 490.415
• Mol file: 127391-18-8.mol

Synonyms:(R)-4-Bromo-4-[(3aS,4R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-butyric acid ethyl ester

Chemical Property of (R)-4-Bromo-4-[(3aS,4R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-butyric acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-Bromo-4-[(3aS,4R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-butyric acid ethyl ester

There total 5 articles about (R)-4-Bromo-4-[(3aS,4R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-butyric acid ethyl 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:

(Z)-5-{(4S,5R)-2,2-Dimethyl-5-[(toluene-4-sulfonylamino)-methyl]-[1,3]dioxolan-4-yl}-pent-4-enoic acid ethyl ester (127731-43-5) → (R)-4-Bromo-4-[(3aS,4R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-butyric acid ethyl ester (127391-18-8)

Guidance literature:

With N-Bromosuccinimide; In 1,2-dimethoxyethane; water; at 0 ℃; for 6h; Yield given;

DOI:10.1016/S0040-4039(00)76180-6

Reference yield:

2,3-O-isopropylidene-L-erythrofuranose (213767-09-0) → (R)-4-Bromo-4-[(3aS,4R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-butyric acid ethyl ester (127391-18-8)

Guidance literature:

Multi-step reaction with 3 steps

2: 2.) KN(SiMe₃)2 / 2.) THF, -78 deg C to 0 deg C

3: NBS / 1,2-dimethoxy-ethane; H₂O / 6 h / 0 °C

With N-Bromosuccinimide; potassium hexamethylsilazane; In 1,2-dimethoxyethane; water;

DOI:10.1016/S0040-4039(00)76180-6

Reference yield:

(3-ethoxycarbonylpropyl)triphenylphosphonium bromide (50479-11-3) → (R)-4-Bromo-4-[(3aS,4R,6aR)-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-butyric acid ethyl ester (127391-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) KN(SiMe₃)2 / 2.) THF, -78 deg C to 0 deg C

2: NBS / 1,2-dimethoxy-ethane; H₂O / 6 h / 0 °C

With N-Bromosuccinimide; potassium hexamethylsilazane; In 1,2-dimethoxyethane; water;

DOI:10.1016/S0040-4039(00)76180-6

upstream raw materials:

(Z)-5-{(4S,5R)-2,2-Dimethyl-5-[(toluene-4-sulfonylamino)-methyl]-[1,3]dioxolan-4-yl}-pent-4-enoic acid ethyl ester

2,3-O-isopropylidene-L-erythrofuranose

(3-ethoxycarbonylpropyl)triphenylphosphonium bromide

N-((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-benzenesulfonamide

Downstream raw materials:

(S)-5-[(3aS,4S,6aR)-2,2-Dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-dihydro-furan-2-one

(1S,2R,8S,8aS)-octahydro-1,2,8-indolizidinetriol