2-O,3-O,5-O-Tribenzyl-D-arabinitol

Base Information

• Chemical Name: 2-O,3-O,5-O-Tribenzyl-D-arabinitol
• CAS No.: 14233-53-5
• Molecular Formula: C₂₆H₃₀O₅
• Molecular Weight: 422.521
• DSSTox Substance ID: DTXSID801274896
• Nikkaji Number: J81.737F
• Mol file: 14233-53-5.mol

Synonyms:14233-53-5;2-O,3-O,5-O-Tribenzyl-D-arabinitol;(2R,3R,4R)-2,3,5-tris(phenylmethoxy)pentane-1,4-diol;SCHEMBL9838648;NJEJAQAZBITKET-TWJOJJKGSA-N;DTXSID801274896;2,3,5-Tris-O-(phenylmethyl)-D-arabinitol

Chemical Property of 2-O,3-O,5-O-Tribenzyl-D-arabinitol

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 422.20932405
• Heavy Atom Count: 31
• Complexity: 441

Purity/Quality:

2,3,5-Tri-O-benzyl-D-arabinitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(C(C(CO)OCC2=CC=CC=C2)OCC3=CC=CC=C3)O
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@H]([C@H]([C@@H](CO)OCC2=CC=CC=C2)OCC3=CC=CC=C3)O
• Uses: 2,3,5-Tri-O-benzyl-D-arabinitol is an intermediate in the synthesis of D-Xylulose 5-Phosphate (X750915). D-Xylulose 5-Phosphate, is a metabolite present in the hexose monophosphate pathway that activates the protein phosphatase 2A.

Technology Process of 2-O,3-O,5-O-Tribenzyl-D-arabinitol

There total 9 articles about 2-O,3-O,5-O-Tribenzyl-D-arabinitol 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: 99.0%

3,4,6-tri-O-benzyl-β-D-arabinofuranoside (60933-68-8) → 3,4,6-tri-O-benzyl-D-arabinitol (14233-53-5)

Guidance literature:

With sodium tetrahydroborate; In ethanol;

DOI:10.3987/COM-97-7939

Reference yield: 98.0%

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → 3,4,6-tri-O-benzyl-D-arabinitol (14233-53-5)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.666667h;

DOI:10.3987/COM-95-7292

Reference yield: 31.0%

methyl 2,3,5-tri-O-benzyl-β-D-arabinofuranoside (79083-44-6) → 3,4,6-tri-O-benzyl-D-arabinitol (14233-53-5)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at 60 ℃; for 1h;

DOI:10.1016/j.carres.2006.05.002

upstream raw materials:

2,3,5-tri-O-benzyl-D-arabinofuranose

2,3,5-tri-O-benzyl-D-xylofuranose

3,4,6-tri-O-benzyl-β-D-arabinofuranoside

methyl 2,3,5-tri-O-benzyl-β-D-arabinofuranoside

Downstream raw materials:

(4R,5S,6R)-5,6-Bis-benzyloxy-4-benzyloxymethyl-[1,3,2]dioxathiepane 2-oxide

(2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentan-2-ol

(2S,3S,4S)-1,3,4-tribenzyloxy-2,5-diiodopentane

1,3,4-tri-O-benzyl-5-O-trityl-D-threo-pentulose

Refernces

• 1、 Jia, Cai,Zhang, Yongmin,Zhang, Li-He,Sinay, Pierre,Sollogoub, Matthieu. "Alkylalanes and methyl furanosides: regioselective O-debenzylation or acetal cleavage". . p. 2135 - 2144. Retrieved 2007/10/03.
• 2、 Yoda, Hidemi,Kawauchi, Miho,Takabe, Kunihiko,Hosoya, Ken. "A short and efficient synthetic process to enantiomerically pure (+)-syributin 1". . p. 1903 - 1906. Retrieved 2007/10/03.