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

Base Information

• Chemical Name: (Z)-5-{(4S,5R)-2,2-Dimethyl-5-[(toluene-4-sulfonylamino)-methyl]-[1,3]dioxolan-4-yl}-pent-4-enoic acid ethyl ester
• CAS No.: 127731-43-5
• Molecular Formula: C₂₀H₂₉NO₆S
• Molecular Weight: 411.519
• Mol file: 127731-43-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (Z)-5-{(4S,5R)-2,2-Dimethyl-5-[(toluene-4-sulfonylamino)-methyl]-[1,3]dioxolan-4-yl}-pent-4-enoic 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:

p-toluenesulfonyl chloride (98-59-9) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

With potassium hexamethylsilazane;

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

Reference yield:

(3-ethoxycarbonylpropyl)triphenylphosphonium bromide (50479-11-3) + N-((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-benzenesulfonamide (127391-20-2) → (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)

Guidance literature:

With potassium hexamethylsilazane; Yield given. Multistep reaction; 2.) THF, -78 deg C to 0 deg C;

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

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) → (1S,2R,8S,8aS)-octahydro-1,2,8-indolizidinetriol (72741-87-8,96648-51-0,96648-52-1,102208-67-3,107982-28-5,111467-60-8,113299-92-6,116497-15-5,148261-04-5,116497-16-6)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 71 percent / SiO₂ / xylene / 48 h / Heating

3: 31 percent / sodium naphtalenide / tetrahydrofuran

4: 86 percent / LiAlH₄ / tetrahydrofuran / 25 °C / Heating

With N-Bromosuccinimide; lithium aluminium tetrahydride; silica gel; sodium naphthalenide; In tetrahydrofuran; 1,2-dimethoxyethane; water; xylene;

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

upstream raw materials:

(3-ethoxycarbonylpropyl)triphenylphosphonium bromide

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

p-toluenesulfonyl chloride

Downstream raw materials:

(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

(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