(2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol
• CAS No.: 140201-56-5
• Molecular Formula: C₃₄H₄₄O₈
• Molecular Weight: 580.719
• Mol file: 140201-56-5.mol

Synonyms:(2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

Chemical Property of (2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

There total 2 articles about (2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol 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: 9.0%

(2S,3R,4S,5R)-3,4,5-Tris(benzyloxy)-2,6-bis(methoxymethoxy)hexanal (140201-53-2) + allyl bromide (106-95-6) → (2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol (140201-56-5) + (2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol (140386-69-2)

Guidance literature:

With chromium chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at -6.5 ℃; for 60h;

DOI:10.1021/jo00037a043

Reference yield:

allyltributylstanane (24850-33-7) + (2S,3R,4S,5R)-3,4,5-Tris(benzyloxy)-2,6-bis(methoxymethoxy)hexanal (140201-53-2) → (2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol (140201-56-5) + (2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol (140386-69-2)

Guidance literature:

With magnesium bromide; In dichloromethane; stereoselectivity; other aldehyde, other allylic compound, other reaction conditions;

DOI:10.1021/jo00037a043

Reference yield:

(2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol (140201-56-5) → (1R,6R,7S,8S,8aS)-1,6,7,8-Tetra-O-benzyloctahydroindolizine (140201-68-9)

Guidance literature:

Multi-step reaction with 10 steps

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

2: 1.) ozone, 2.) PPh₃ / 1.) CH₂Cl₂

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

4: 85 percent / PPh₃, DEAD / tetrahydrofuran / a) 0 deg C to r.t., b) r.t., 24 h

5: 97 percent / 25percent HCl / methanol / 2 h / 60 °C

6: 81 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

7: 91 percent / DMAP, pyridine / a) 0 deg C, 1 h, b) 0 deg C to r.t., c) r.t., 18 h

8: hydrazine-hydrate / ethanol / 5 h / Heating

9: 88 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

10: 78 percent / NEt₃, PPh₃ / CCl₄; acetonitrile / a) 0 deg C to r.t., b) r.t., 35 h

With pyridine; 1H-imidazole; hydrogenchloride; dmap; 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:

allyltributylstanane

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

allyl bromide

Downstream raw materials:

(2R,3S,4R,5R,6R)-2,3,4,6-Tetra-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol

(2R,3S,4S,5R,6R)-2,3,4,6-Tetra-O-benzyl-1,2,3,4,5,6-hexahydroxy-8-N-phthaloyloctan-8-amine

(2S,3R,1'S,2'S,3'R)-3-Benzyloxy-2-<1',2',3'-tris(benzyloxy)-4'-<(tert-butyldiphenylsilyl)oxy>butyl>pyrrolidine

(2R,3S,4R,5R,6R)-2,3,4,6-Tetra-O-benzyl-1,2,3,4,5,6-hexahydroxy-1,5-bis-O-(methoxymethyl)-8-N-phthaloyloctan-8-amine