methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate

Base Information

• Chemical Name: methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate
• CAS No.: 150674-67-2
• Molecular Formula: C₂₀H₂₉NO₆S
• Molecular Weight: 411.519
• Mol file: 150674-67-2.mol

Synonyms:methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate

Chemical Property of methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate

There total 20 articles about methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate 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: 86.0%

methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-[(4-methylphenyl)sulfonyl]-α-phenylsulfonyl]-3-pyrrolidineacetate (188569-97-3) → methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate (150674-67-2)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at 0 ℃; for 4h;

DOI:10.1016/S0040-4020(00)00579-2

Reference yield: 72.0%

(2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine (150674-66-1) + Methylenetriphenylphosphorane (19493-09-5) → methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate (150674-67-2)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(00)79176-3

Reference yield:

(S)-N-[1-(methoxy)methoxy-3-buten-2-yl]-4-methylbenzenesulfonamide (150674-62-7) → methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate (150674-67-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / DEAD, Ph₃P

2: 41 percent / AIBN / benzene / 6 h / Heating

3: 85 percent / oxone / H₂O; methanol / 0 --> 20 deg C

4: 89 percent / 1.) MeLi / tetrahydrofuran / 1.) 78 deg C; 2.) 0 deg C

5: 60 percent / 5percent Na-Hg / methanol / 0 °C

With Oxone; sodium amalgam; 2,2'-azobis(isobutyronitrile); methyllithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; benzene;

DOI:10.1055/s-1997-784

upstream raw materials:

(2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine

Methylenetriphenylphosphorane

methyl [2S-(2α,3β,4β)]-[2-(methoxymethoxy)methyl-4-(1-methylethenyl)-1-[(4-methylphenyl)sulfonyl]-α-phenylsulfonyl]-3-pyrrolidineacetate

(E)-3-Methyl-4-(thiophenoxy)-2-buten-1-ol

Downstream raw materials:

(-)-kainic acid

(2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

(2S,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

methyl [2S-(2α,3β,4β)]-[2-(methoxycarbonyl)-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate