(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

Base Information

Chemical Name:(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol
CAS No.:869660-99-1
Molecular Formula:C₂₀H₃₁NO₆
Molecular Weight:381.469
Hs Code.:

Synonyms:(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

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Chemical Property of (2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

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Technology Process of (2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

There total 12 articles about (2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 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: 83.0%

: 869660-98-0
(2R,3R,4S)-1-O-benzyl-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

: 869660-99-1
(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

Guidance literature:: With ammonia; lithium; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/j.tetasy.2005.08.039

Reference yield:

: 869660-95-7
1-O-benzyl-2,3-O-isopropylidene-4-oxiranyl-D-arabinitol

: 869660-99-1
(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 6 steps

1.1: magnesium; iodine / tetrahydrofuran

1.2: 86 percent / copper(I) iodide / tetrahydrofuran / 0 - 20 °C

2.1: triethylamine / CH₂Cl₂ / 1 h / 20 °C

3.1: 550 mg / sodium azide; 18-crown-6 / dimethylsulfoxide / 24 h / 65 °C

4.1: LiAlH₄ / tetrahydrofuran / 0 - 20 °C

5.1: 450 mg / triethylamine / tetrahydrofuran / 6 h / 20 °C

6.1: 83 percent / lithium; liq. ammonia / tetrahydrofuran / 0.5 h / -78 °C

With lithium aluminium tetrahydride; sodium azide; 18-crown-6 ether; ammonia; iodine; lithium; magnesium; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1.2: Crignard reaction;
DOI:10.1016/j.tetasy.2005.08.039

Reference yield:

: 869660-96-8
(2R,3R,4R)-1-O-benzyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3,4-tetrol

: 869660-99-1
(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 5 steps

1: triethylamine / CH₂Cl₂ / 1 h / 20 °C

2: 550 mg / sodium azide; 18-crown-6 / dimethylsulfoxide / 24 h / 65 °C

3: LiAlH₄ / tetrahydrofuran / 0 - 20 °C

4: 450 mg / triethylamine / tetrahydrofuran / 6 h / 20 °C

5: 83 percent / lithium; liq. ammonia / tetrahydrofuran / 0.5 h / -78 °C

With lithium aluminium tetrahydride; sodium azide; 18-crown-6 ether; ammonia; lithium; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tetasy.2005.08.039