2,3,4-Tri-O-benzyl-beta-L-arabinopyranose

Base Information

• Chemical Name: 2,3,4-Tri-O-benzyl-beta-L-arabinopyranose
• CAS No.: 77943-33-0
• Molecular Formula: C26H28 O5
• Molecular Weight: 420.5
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID40428648
• Mol file: 77943-33-0.mol

Synonyms:77943-32-9;(2R,3R,4S,5R)-3,4,5-Tris(benzyloxy)tetrahydro-2H-pyran-2-ol;77943-33-0;DTXSID40428648;2,3,4-Tri-O-benzyl- beta -L-arabinopyranose

Chemical Property of 2,3,4-Tri-O-benzyl-beta-L-arabinopyranose

Chemical Property:

• Vapor Pressure: 1.2E-13mmHg at 25°C
• Melting Point: 76-79°C
• Refractive Index: 1.609
• Boiling Point: 566oC at 760 mmHg
• Flash Point: 296.1oC
• PSA: 57.15000
• Density: 1.21g/cm3
• LogP: 4.09120
• Water Solubility.: Insoluble in water.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 420.19367399
• Heavy Atom Count: 31
• Complexity: 482

Purity/Quality:

99% ^*data from raw suppliers

2,3,4-Tri-O-benzyl-b-L-arabinopyranose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(O1)O)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H](O1)O)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Uses: 2,3,4-Tri-O-benzyl-beta-L-arabinopyranose is used as a pharmaceutical intermediate.

Technology Process of 2,3,4-Tri-O-benzyl-beta-L-arabinopyranose

There total 55 articles about 2,3,4-Tri-O-benzyl-beta-L-arabinopyranose 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: 85.0%

benzyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside (1044833-49-9) → 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)

Guidance literature:

With hydrogenchloride; In acetonitrile; at 80 ℃; for 22h;

DOI:10.1080/07328300802030878

Reference yield: 80.0%

benzyl 2,3,4-tri-O-benzyl-β-L-arabinopyranoside (7494-97-5) → 2,3,4-tri-O-benzyloxy-L-arabinopyranose (18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1)

Guidance literature:

With hydrogenchloride; In acetonitrile; at 80 ℃; for 22h;

DOI:10.1080/07328300802030878

Reference yield: 80.0%

2-methoxyethyl 2,3,4-tri-O-benzyl-β-D-xylopyranoside (87908-24-5) → 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)

Guidance literature:

With titanium tetrachloride; In dichloromethane; for 0.0833333h; Ambient temperature;

DOI:10.1246/bcsj.62.3549

upstream raw materials:

benzyl 2,3,4-tri-O-benzyl-α-L-arabinopyranoside

benzyl 2,3,4-tri-O-benzyl-β-L-arabinopyranoside

(3R,4S,5S)-3,4,5-Tris-benzyloxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran

2-methoxyethyl 2,3,4-tri-O-benzyl-α-L-arabinopyranoside

Downstream raw materials:

5,6,7-Tri-O-benzyl-2,2,3,3-tetradehydro-2,3-dideoxy-D-ido-octose Diethyl Acetal

ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-L-serine

ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-L-serine

O-(2,3,4-Tri-O-benzyl-D-xylopyranosyl)-N,2,2-tris(4-chlorphenyl)acetimidat

Refernces

• 1、 Ye, Hui,Xiao, Cong,Zhou, Quan-Quan,Wang, Peng George,Xiao, Wen-Jing. "Synthesis of Phenolic Glycosides: Glycosylation of Sugar Lactols with Aryl Bromides via Dual Photoredox/Ni Catalysis". . p. 13325 - 13334. Retrieved 2018/11/02.
• 2、 Nifant'ev, Ilya E.,Shlyakhtin, Andrey V.,Bagrov, Vladimir V.,Ezhov, Roman N.,Lozhkin, Boris A.,Churakov, Andrei V.,Ivchenko, Pavel V.. "Ring-opened 4-hydroxy-δ-valerolactone subunit as a key structural fragment of polyesters that degrade without acid formation". . p. 629 - 631. Retrieved 2018/12/13.