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

Base Information

• Chemical Name: (S_S,2S,3S)-(+)-N-(4-benzyloxy-2,3-isopropylidenedioxy)butyrylidene-p-toluenesulfinamide
• CAS No.: 1029251-05-5
• Molecular Formula: C₂₁H₂₅NO₄S
• Molecular Weight: 387.5

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

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

Chemical Property:

Purity/Quality:

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

There total 1 articles about (S_S,2S,3S)-(+)-N-(4-benzyloxy-2,3-isopropylidenedioxy)butyrylidene-p-toluenesulfinamide 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: 48.0%

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) + (S)-p-toluenesulfinimide (188447-91-8) → (SS,2S,3S)-(+)-N-(4-benzyloxy-2,3-isopropylidenedioxy)butyrylidene-p-toluenesulfinamide (1029251-05-5)

Guidance literature:

With titanium(IV) tetraethanolate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo020302e

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:

(SS,2S,3S)-(+)-N-(4-benzyloxy-2,3-isopropylidenedioxy)butyrylidene-p-toluenesulfinamide (1029251-05-5) → (2S,3S,4S)-(-)-5-benzyloxy-3,4-dihydroxy-2-aminopentanoic acid hydrochloride

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 67 percent / tetrahydrofuran; toluene / 22 h / -78 - 20 °C

2.1: 95 percent / hydrogen chloride; water / diethyl ether / 12 h / 20 °C

With hydrogenchloride; water; isopropyl alcohol; In tetrahydrofuran; diethyl ether; toluene; 1.2: Strecker synthesis;

DOI:10.1021/jo020302e

upstream raw materials:

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

(S)-p-toluenesulfinimide

Downstream raw materials:

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

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