Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl ester
• CAS No.: 617700-51-3
• Molecular Formula: C₂₅H₃₂N₂O₁₁S₂
• Molecular Weight: 600.668
• Mol file: 617700-51-3.mol

Synonyms:Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl ester

Chemical Property of Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl ester

There total 19 articles about Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl 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: 80.0%

Dimethoxymethane (109-87-5) + (2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine (617700-50-2) → Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl ester (617700-51-3)

Guidance literature:

With phosphorus pentoxide; at 20 ℃; for 1.5h;

DOI:10.1002/chem.200400830

Reference yield: 80.0%

2,2-dimethoxy-propane (77-76-9) + (2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine (617700-50-2) → Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl ester (617700-51-3)

Guidance literature:

With phosphorus pentoxide;

DOI:10.1055/s-2003-39314

Reference yield:

(3E,5S,6S,7S)-8-[(tert-butyldimethylsilyl)oxy]-6,7-(isopropylidenedioxy)-5-[(2-nitrobenzenesulfonyl)amino]-oct-3-ene (617700-45-5) → Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl ester (617700-51-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / diethyl azodicarboxylate; PPh₃ / benzene; toluene / 7 h / 20 °C

2: 92 percent / Cl₂Ru(PCy₃)2=CHPh / benzene / 1.5 h / 60 °C

3: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran; acetonitrile / 6 h / 20 °C

4: 91 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

5: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 50 °C

6: 80 percent / P₂O₅ / 1.5 h / 20 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; phosphorus pentoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1002/chem.200400830

upstream raw materials:

2,2-dimethoxy-propane

(2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine

Dimethoxymethane

Carbamic acid (E)-(S)-3-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-ethyl-allyl ester

Downstream raw materials:

(+)-lentiginosine