(2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol

Base Information

• Chemical Name: (2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol
• CAS No.: 716163-47-2
• Molecular Formula: C₁₈H₂₃N₃O₅
• Molecular Weight: 361.398
• Mol file: 716163-47-2.mol

Synonyms:(2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol

Chemical Property of (2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol

There total 1 articles about (2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol 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: 62.0%

propynoic acid methyl ester (922-67-8) + (2S,3S)-4-azido-3-benzyloxy-1,2-O-isopropylidene-1,2-butanediol (143365-04-2,1228077-93-7) → (2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(5-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol + (2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol (716163-47-2)

Guidance literature:

In toluene; for 4h; Heating;

DOI:10.1016/j.tetasy.2004.03.025

Reference yield: 69.0%

(2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol (716163-47-2) → (2S,3S)-3-benzyloxy-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol (716163-73-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃; for 24h;

DOI:10.1016/j.tetasy.2004.03.025

Reference yield:

(2S,3S)-3-benzyloxy-1,2-O-isopropylidene-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol (716163-47-2) → 1-(2-benzyloxy-3-oxo-propyl)-1H-[1,2,3]triazole-4-carboxylic acid methyl ester (716164-01-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / HCl / H₂O; dioxane / 24 h / 20 °C

2: NaIO₄; NaHCO₃ / CHCl₃; H₂O / 3 h / 40 °C

With hydrogenchloride; sodium periodate; sodium hydrogencarbonate; In 1,4-dioxane; chloroform; water;

DOI:10.1016/j.tetasy.2004.03.025

upstream raw materials:

propynoic acid methyl ester

(2S,3S)-4-azido-3-benzyloxy-1,2-O-isopropylidene-1,2-butanediol

Downstream raw materials:

(2S,3S)-3-benzyloxy-4-(4-methoxycarbonyl-1,2,3-triazol-1-yl)-1,2-butanediol

1-(2-benzyloxy-3-oxo-propyl)-1H-[1,2,3]triazole-4-carboxylic acid methyl ester

dimethyl (1S,2S)-2-benzyloxy-1-hydroxy-3-(4-methoxycarbonyl-1,2,3-triazol-1-yl)propylphosphonate

dimethyl (1R,2S)-2-benzyloxy-1-hydroxy-3-(4-methoxycarbonyl-1,2,3-triazol-1-yl)propylphosphonate