3,4,6-TRI-O-BENZYL-2-DEOXY-D-GLUCOPYRANOSE

Base Information

• Chemical Name: 3,4,6-TRI-O-BENZYL-2-DEOXY-D-GLUCOPYRANOSE
• CAS No.: 132732-60-6
• Molecular Formula: C27H30 O5
• Molecular Weight: 434.52
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID60450284
• Nikkaji Number: J897.632E
• Mol file: 132732-60-6.mol

Synonyms:2DEOXYDGLUCOPYRANOSE3,4,6TRIBENZYLETHER

Chemical Property of 3,4,6-TRI-O-BENZYL-2-DEOXY-D-GLUCOPYRANOSE

Chemical Property:

• Melting Point: 103.0 to 107.0 °C
• Boiling Point: 600.7±55.0 °C(Predicted)
• PKA: 13.37±0.20(Predicted)
• PSA: 57.15000
• Density: 1.161±0.06 g/cm3(Predicted)
• LogP: 4.48130
• Storage Temp.: Refrigerator
• Solubility.: slightly sol. in Dioxane
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 434.20932405
• Heavy Atom Count: 32
• Complexity: 496

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,4,6-Tri-O-benzyl-2-deoxy-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(OC1O)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: C1[C@H]([C@@H]([C@H](OC1O)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of 3,4,6-TRI-O-BENZYL-2-DEOXY-D-GLUCOPYRANOSE

There total 1 articles about 3,4,6-TRI-O-BENZYL-2-DEOXY-D-GLUCOPYRANOSE 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: 98.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 3,4,6-tri-O-benzyl-2-deoxy-D-glucose (132732-60-6,94189-64-7)

Guidance literature:

3,4,6-tri-O-benzyl-D-glucal; With N-iodo-succinimide; In water; acetonitrile; at 0 - 20 ℃; for 0.25h;

With sodium dithionite; sodium hydrogencarbonate; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.05.043

Reference yield: 80.0%

3,4,6-tri-O-benzyl-2-deoxy-D-glucose (132732-60-6,94189-64-7) + Methyltriphenylphosphonium bromide (1779-49-3) → (2R,3R,4R)-1,3,4-Tris-benzyloxy-hept-6-en-2-ol (157736-63-5)

Guidance literature:

With n-butyllithium; at 0 - 20 ℃; for 16h;

DOI:10.1016/j.tetlet.2005.05.043

Reference yield:

3,4,6-tri-O-benzyl-2-deoxy-D-glucose (132732-60-6,94189-64-7) → (5S,7R,8S,9R)-8,9-Bis-benzyloxy-7-benzyloxymethyl-3,6-dioxa-2-thia-1-aza-spiro[4.5]decane 2,2-dioxide

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / n-BuLi / 16 h / 0 - 20 °C

2: 72 percent / I₂; aq. NaHCO₃ / diethyl ether / 16 h

3: 55 percent / toluene / 15 h / 50 °C

4: 95 percent / NaOMe / methanol / 3 h

5: 90 percent / sulfamoyl chloride; pyridine / CH₂Cl₂ / 16 h

6: MgO; PhI(OAc)2 / Rh₂(OAc)4 / CH₂Cl₂ / 16 h / Heating

With pyridine; n-butyllithium; [bis(acetoxy)iodo]benzene; sulphamoyl chloride; iodine; sodium methylate; magnesium oxide; sodium hydrogencarbonate; dirhodium tetraacetate; In methanol; diethyl ether; dichloromethane; toluene; 1: Wittig reaction / 6: Du Bois reaction;

DOI:10.1016/j.tetlet.2005.05.043

upstream raw materials:

3,4,6-tri-O-benzyl-D-glucal

Downstream raw materials:

(2R,3R,4R)-1,3,4-Tris-benzyloxy-hept-6-en-2-ol

Refernces