(Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane

Base Information

• Chemical Name: (Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane
• CAS No.: 150640-12-3
• Molecular Formula: C₁₄H₁₇NO₄S
• Molecular Weight: 295.359
• Mol file: 150640-12-3.mol

Synonyms:(Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane

Chemical Property of (Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane

There total 1 articles about (Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane 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:

<(4-methylphenyl)thio>nitromethane (150640-22-5) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane (150640-12-3)

Guidance literature:

With potassium tert-butylate; methanesulfonyl chloride; triethylamine; Yield given. Multistep reaction; 1.) t-BuOH, THF, 0 deg C, 2.) t-BuOH, THF, from -78 deg C to 0 deg C;

DOI:10.1039/c39930000889

Reference yield: 71.0%

(Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane (150640-12-3) → (2'R,3'R,4R)-2,2-dimethyl-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane (150737-92-1) + (2'S,3'S,4R)-2,2-dimethyl-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane (150640-13-4)

Guidance literature:

With tert.-butylhydroperoxide; n-butyllithium; In hexane; toluene; at -78 ℃; for 1h; Yields of byproduct given;

DOI:10.1021/jo00125a032

Reference yield:

(Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane (150640-12-3) → S-(4''-methylphenyl) (1''S,2'R,4S)-2'-amino>-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanethioate

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / n-BuLi, t-BuOOH / hexane; toluene / 1 h / -78 °C

2: 87 percent / NaHCO₃ / CH₂Cl₂ / 48 h / Ambient temperature

With tert.-butylhydroperoxide; n-butyllithium; sodium hydrogencarbonate; In hexane; dichloromethane; toluene;

DOI:10.1021/jo00125a032

upstream raw materials:

<(4-methylphenyl)thio>nitromethane

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(2'R,3'R,4R)-2,2-dimethyl-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

(2'S,3'S,4R)-2,2-dimethyl-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

(R)-Amino-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-thioacetic acid S-p-tolyl ester

S-(4''-methylphenyl) (2'R,4S)-2'-<(benzyloxycarbonyl)amino>-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanethioate