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

Base Information

• Chemical Name: (2R,3S,4R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)hex-5-enal
• CAS No.: 851542-24-0
• Molecular Formula: C₃₇H₄₀O₅
• Molecular Weight: 564.722
• Mol file: 851542-24-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (2R,3S,4R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)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:

C39H46O4S2 (851542-23-9) + vinyl magnesium bromide (1826-67-1) → (2R,3S,4R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)hex-5-enal (851542-24-0)

Guidance literature:

C₃₉H₄₆O₄S₂; With water; mercury dichloride; mercury(II) oxide; In acetonitrile; Inert atmosphere;

vinyl magnesium bromide; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1039/c0ob00475h

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (2R,3S,4R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)hex-5-enal (851542-24-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / Inert atmosphere

1.2: Inert atmosphere

2.1: potassium tert-butylate / benzene / Inert atmosphere

3.1: water; mercury dichloride; mercury(II) oxide / acetonitrile / Inert atmosphere

3.2: 0 °C / Inert atmosphere

With potassium tert-butylate; water; trifluoroacetic acid; mercury dichloride; mercury(II) oxide; In acetonitrile; benzene;

DOI:10.1039/c0ob00475h

Reference yield: 60.0%

(2R,3S,4R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)hex-5-enal (851542-24-0) → (1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol (99695-34-8) + (1S,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol (213400-35-2)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; Overall yield = 85 %; Overall yield = 3.19 g; diastereoselective reaction; Reflux;

DOI:10.1016/j.tet.2013.09.098

upstream raw materials:

C₃₉H₄₆O₄S₂

vinyl magnesium bromide

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

(1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

(1S,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-en-1-yl phosphate

dibenzyl (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-[(benzyloxy)methyl]cyclohex-2-en-1-yl phosphate