(2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone

Base Information

• Chemical Name: (2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone
• CAS No.: 343934-66-7
• Molecular Formula: C₃₃H₃₃BrN₂O₃
• Molecular Weight: 585.541
• Mol file: 343934-66-7.mol

Synonyms:(2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone

Chemical Property of (2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone

There total 4 articles about (2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone 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: 82.0%

2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose (73111-58-7,130861-06-2,73111-15-6) + 4-bromophenylhydrazine hydrochloride (622-88-8,41931-18-4) → (2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone (343934-66-7)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane;

DOI:10.1016/S0957-4166(01)00050-7

Reference yield:

2,3,4-tri-O-benzyl-D-xylo-pentodialdose 1,1-diethyl dithioacetal (116384-32-8) → (2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone (343934-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BuLi / toluene; hexane / 1 h / 0 °C

1.2: 2.3 g / toluene / 2 h / 0 °C

2.1: 77 percent / NBS; CdCO₃ / acetone; H₂O / 0.67 h

3.1: 82 percent / aq. NaHCO₃ / CH₂Cl₂

With N-Bromosuccinimide; n-butyllithium; cadmium(II) carbonate; sodium hydrogencarbonate; In hexane; dichloromethane; water; acetone; toluene; 1.2: Wittig reaction;

DOI:10.1016/S0957-4166(01)00050-7

Reference yield:

2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal (108713-90-2) → (2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone (343934-66-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridinium chlorochromate / CH₂Cl₂

2.1: BuLi / toluene; hexane / 1 h / 0 °C

2.2: 2.3 g / toluene / 2 h / 0 °C

3.1: 77 percent / NBS; CdCO₃ / acetone; H₂O / 0.67 h

4.1: 82 percent / aq. NaHCO₃ / CH₂Cl₂

With N-Bromosuccinimide; n-butyllithium; cadmium(II) carbonate; sodium hydrogencarbonate; pyridinium chlorochromate; In hexane; dichloromethane; water; acetone; toluene; 2.2: Wittig reaction;

DOI:10.1016/S0957-4166(01)00050-7

upstream raw materials:

2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose

4-bromophenylhydrazine hydrochloride

2,3,4-tri-O-benzyl-D-xylo-pentodialdose 1,1-diethyl dithioacetal

2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal