(S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile

Base Information

• Chemical Name: (S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile
• CAS No.: 476486-33-6
• Molecular Formula: C₂₂H₂₆N₂O₄S
• Molecular Weight: 414.525

Synonyms:(S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile

Chemical Property of (S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile

Chemical Property:

Purity/Quality:

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Technology Process of (S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile

There total 3 articles about (S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile 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: 67.0%

diethylaluminium cyanide (5804-85-3) + (SS,2S,3S)-(+)-N-(4-benzyloxy-2,3-isopropylidenedioxy)butyrylidene-p-toluenesulfinamide (1029251-05-5) → (SS,2S,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile + (SS,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile (476486-33-6)

Guidance literature:

diethylaluminium cyanide; With isopropyl alcohol; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 0.333333h;

(S_S,2S,3S)-(+)-N-(4-benzyloxy-2,3-isopropylidenedioxy)butyrylidene-p-toluenesulfinamide; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 22h; Further stages.;

DOI:10.1021/jo020302e

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → (SS,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile (476486-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 48 percent / titanium tetraethoxide / CH₂Cl₂ / 3 h / 20 °C

2.1: isopropanol / tetrahydrofuran; toluene / 0.33 h / -78 - 20 °C

2.2: 67 percent / tetrahydrofuran; toluene / 22 h / -78 - 20 °C

With titanium(IV) tetraethanolate; isopropyl alcohol; In tetrahydrofuran; dichloromethane; toluene; 2.2: Strecker synthesis;

DOI:10.1021/jo020302e

Reference yield:

(S)-p-toluenesulfinimide (188447-91-8) → (SS,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-3,4-isopropylidenedioxy-5-benzyloxypentane nitrile (476486-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 48 percent / titanium tetraethoxide / CH₂Cl₂ / 3 h / 20 °C

2.1: isopropanol / tetrahydrofuran; toluene / 0.33 h / -78 - 20 °C

2.2: 67 percent / tetrahydrofuran; toluene / 22 h / -78 - 20 °C

With titanium(IV) tetraethanolate; isopropyl alcohol; In tetrahydrofuran; dichloromethane; toluene; 2.2: Strecker synthesis;

DOI:10.1021/jo020302e

upstream raw materials:

diethylaluminium cyanide

(S_S,2S,3S)-(+)-N-(4-benzyloxy-2,3-isopropylidenedioxy)butyrylidene-p-toluenesulfinamide

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

(S)-p-toluenesulfinimide

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