(S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-5-tert-butyldiphenylsilyloxy-3,4-isopropylidenedioxypentane nitrile

Base Information

• Chemical Name: (S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-5-tert-butyldiphenylsilyloxy-3,4-isopropylidenedioxypentane nitrile
• CAS No.: 476486-34-7
• Molecular Formula: C₃₁H₃₈N₂O₄SSi
• Molecular Weight: 562.805

Synonyms:(S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-5-tert-butyldiphenylsilyloxy-3,4-isopropylidenedioxypentane nitrile

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about (S_S,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-5-tert-butyldiphenylsilyloxy-3,4-isopropylidenedioxypentane 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: 71.0%

diethylaluminium cyanide (5804-85-3) + (SS,2S,3S)-(+)-N-(4-tert-butyldiphenylsilyloxy-2,3-isopropylidenedioxy)butyrylidene-p-toluenesulfinamide → (SS,2S,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-5-tert-butyldiphenylsilyloxy-3,4-isopropylidenedioxypentane nitrile + (SS,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-5-tert-butyldiphenylsilyloxy-3,4-isopropylidenedioxypentane nitrile (476486-34-7)

Guidance literature:

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

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

DOI:10.1021/jo020302e

Reference yield:

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose (101331-92-4) → (SS,2R,3S,4S)-(+)-N-(p-toluenesulfinyl)-2-amino-5-tert-butyldiphenylsilyloxy-3,4-isopropylidenedioxypentane nitrile (476486-34-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 59 percent / titanium tetraethoxide / CH₂Cl₂ / 3 h / 20 °C

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

2.2: 71 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-5-tert-butyldiphenylsilyloxy-3,4-isopropylidenedioxypentane nitrile (476486-34-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 59 percent / titanium tetraethoxide / CH₂Cl₂ / 3 h / 20 °C

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

2.2: 71 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

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose

(S)-p-toluenesulfinimide

Downstream raw materials:

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

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