(2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal

Base Information Edit

Chemical Name:(2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal
CAS No.:195873-65-5
Molecular Formula:C₂₇H₂₈O₄
Molecular Weight:416.517
Hs Code.:
Mol file:195873-65-5.mol

Synonyms:(2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal

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Chemical Property of (2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal Edit

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Technology Process of (2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal

There total 4 articles about (2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal 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:

: 195873-64-4
3,4,5-tri-O-benzyl-1,2-dideoxy-D-xylohept-1-enitol

: 195873-65-5
(2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 0.333333h;
DOI:10.1016/S0040-4039(97)01513-X

Reference yield:

: 18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1
2,3,4-tri-O-benzyl-D-xylopyranose

: 195873-65-5
(2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal

Guidance literature:: Multi-step reaction with 2 steps

1.1: BuLi / tetrahydrofuran; pentane / 2 h / 20 °C

1.2: 80 percent / tetrahydrofuran; pentane / Heating

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; pentane; 1.2: Wittig methylenation / 2.1: Swern oxidation;
DOI:10.1021/jo0607562

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 195873-65-5
(2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal

Guidance literature:: Multi-step reaction with 5 steps

1.1: SOCl₂ / 4 h / Heating

2.1: NaH; Bu₄NI / dimethylformamide / 0.5 h / 0 °C

3.1: 71 percent / H₂SO₄ / acetic acid; dioxane

4.1: BuLi / tetrahydrofuran; pentane / 2 h / 20 °C

4.2: 80 percent / tetrahydrofuran; pentane / Heating

5.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With n-butyllithium; thionyl chloride; oxalyl dichloride; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid; N,N-dimethyl-formamide; pentane; 4.2: Wittig methylenation / 5.1: Swern oxidation;
DOI:10.1021/jo0607562