(2R,3S,4R,5R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol

Base Information

• Chemical Name: (2R,3S,4R,5R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol
• CAS No.: 140201-52-1
• Molecular Formula: C₃₂H₄₀O₇
• Molecular Weight: 536.665
• Mol file: 140201-52-1.mol

Synonyms:(2R,3S,4R,5R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol

Chemical Property of (2R,3S,4R,5R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol

There total 2 articles about (2R,3S,4R,5R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol 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: 87.0%

chloromethyl methyl ether (107-30-2) + (2R,3S,4S,5R/S)-2,3,4-Tri-O-benzyl-6-heptene-1,2,3,4,5-pentol (140201-51-0,140386-66-9) → (2R,3S,4R,5S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol (140386-67-0) + (2R,3S,4R,5R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol (140201-52-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 24h;

DOI:10.1021/jo00037a043

Reference yield:

2,3,4-tri-O-benzyl-D-xylopyranose (18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1) → (2R,3S,4R,5R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol (140201-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / tetrahydrofuran / 48 h / Ambient temperature

2: 82 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 24 h

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00037a043

Reference yield:

(2R,3S,4R,5R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-6-heptene-1,2,3,4,5-pentol (140201-52-1) → (1S,6R,7S,8S,8aS)-1,6,7,8-Tetra-O-benzyloctahydroindolizine (140386-79-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) ozone, 2.) PPh₃ / 1.) CH₂Cl₂, 2.) a) -78 deg C, 1 h, b) r.t., 2h

2: 9 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 60 h / -6.5 °C

3: 1. NaH / 1.) DMF, 2.) DMF, r.t., 24 h

4: 1.) ozone, 2.) PPh₃ / 1.) CH₂Cl₂

5: LiAlH₄ / diethyl ether / 24 h / 0 deg C to r.t.

6: 93 percent / PPh₃, DEAD / tetrahydrofuran / a) 0 deg C to r.t., b) r.t., 24 h

7: 92 percent / 25percent HCl / methanol / 2 h / 60 °C

8: 92 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

9: 98 percent / DMAP, pyridine / a) 0 deg C, 1 h, b) 0 deg C to r.t., c) r.t., 18 h

10: 94 percent / hydrazine-hydrate / ethanol / 5 h / Heating

11: 88 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

12: 66 percent / NEt₃, PPh₃ / CCl₄; acetonitrile / a) 0 deg C to r.t., b) r.t., 35 h

With pyridine; 1H-imidazole; hydrogenchloride; dmap; chromium chloride; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; ozone; hydrazine hydrate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00037a043

upstream raw materials:

chloromethyl methyl ether

(2R,3S,4S,5R/S)-2,3,4-Tri-O-benzyl-6-heptene-1,2,3,4,5-pentol

2,3,4-tri-O-benzyl-D-xylopyranose

Downstream raw materials:

(2S,3R,4S,5R)-3,4,5-Tris(benzyloxy)-2,6-bis(methoxymethoxy)hexanal

(1S,6S,7R,8S,8aS)-1,6,7,8-Tetra-O-benzyloctahydroindolizin-5-one

(2S,3R,4S)-2,3,4-Tris-benzyloxy-4-((2S,3S)-3-benzyloxy-pyrrolidin-2-yl)-butyric acid

(2S,3S,1'S,2'R,3'S)-3-(Benzyloxy)-2-<1',2',3'-tris(benzyloxy)-4'-oxobutyl>-N-(trifluoroacetyl)pyrrolidine