(1S,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol

Base Information

• Chemical Name: (1S,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol
• CAS No.: 474799-74-1
• Molecular Formula: C₃₆H₃₈N₂O₅S
• Molecular Weight: 610.774

Synonyms:(1S,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol

Chemical Property of (1S,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol

There total 2 articles about (1S,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol 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: 55.0%

2-bromo-1,3-thiazole (3034-53-5,215777-74-5) + 1-(N-benzylhydroxylamino)-2,3,5-tri-O-benzyl-1-deoxy-L-xylose (474799-73-0) → (1S,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol (474799-74-1) + (1R,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol

Guidance literature:

2-bromo-1,3-thiazole; With n-butyllithium; In diethyl ether; hexane; at -78 - -70 ℃;

1-(N-benzylhydroxylamino)-2,3,5-tri-O-benzyl-1-deoxy-L-xylose; In tetrahydrofuran; diethyl ether; hexane; at -70 ℃; for 5h; Further stages.;

DOI:10.1021/jo020252d

Reference yield:

2,3,5-tri-O-benzyl-L-xylofuranose (16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3) → (1S,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol (474799-74-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 0.75 h / 110 °C

2: nBuLi / diethyl ether; tetrahydrofuran / 5 h / -70 - -65 °C

With n-butyllithium; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4020(03)00631-8

Reference yield:

(1S,2R,3R,4S)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol (474799-74-1) → (1S,2R,3R,4S)-1-N-benzylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol (474799-75-2)

Guidance literature:

With copper diacetate; acetic acid; zinc; In water; at 20 - 70 ℃; for 1h;

DOI:10.1016/S0040-4020(03)00631-8

upstream raw materials:

2-bromo-1,3-thiazole

1-(N-benzylhydroxylamino)-2,3,5-tri-O-benzyl-1-deoxy-L-xylose

2,3,5-tri-O-benzyl-L-xylofuranose

Downstream raw materials:

(1S,2R,3R,4S)-1-N-benzylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol

(2S,3R,4R,5R)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)pyrrolidine

(2S,3R,4R,5R)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde

N-benzyl-3,4,6-tri-O-benzyl-2,5-dideoxy-2,5-imino-D-mannitol

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