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.: 160549-11-1
• Molecular Formula: C₂₇H₃₀O₅
• Molecular Weight: 434.532
• DSSTox Substance ID: DTXSID60450284
• Nikkaji Number: J897.632E

Synonyms:3,4,6-Tri-O-benzyl-2-deoxy-D-glucopyranose;132732-60-6;160549-11-1;(4R,5S,6R)-4,5-Bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol;(4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol;MFCD06797170;SCHEMBL17867767;DTXSID60450284;PDGHLARNGSMEJE-GWDBROLASA-N;AKOS025405266;CS-0447520;T1933;2-deoxy-3,4,6-tri-O-benzyl-d-glucopyranose;6-O-(A-D-MALTOTRIOSYL)-D-GLUCOPYRANOSE;V10102;3-O,4-O,6-O-Tribenzyl-2-deoxy-D-glucopyranose;3,4,6-Tri-O-benzyl-2-deoxy-D-glucopyranose, 95%;W-201084;(4R,5S,6R)-4,5-BIS(BENZYLOXY)-6-[(BENZYLOXY)METHYL]OXAN-2-OL

Chemical Property of 3,4,6-Tri-O-benzyl-2-deoxy-D-glucopyranose

Chemical Property:

• 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%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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 22 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: 90.0%

[2-((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-trimethyl-silane (81336-84-7,81336-93-8) → 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose (160549-11-1)

Guidance literature:

With lithium tetrafluoroborate; In acetonitrile; at 70 ℃; 3-8 h;

DOI:10.1016/S0040-4039(01)82992-0

Reference yield: 89.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose (160549-11-1)

Guidance literature:

With benzyl chloromethyl sulfide; water; potassium iodide; In acetonitrile; at 0 ℃; for 1h;

Reference yield: 85.0%

methyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-hexopyranoside (74545-14-5) → 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose (160549-11-1)

Guidance literature:

With hydrogenchloride; In acetic acid; for 5h; Heating;

DOI:10.1016/0008-6215(94)84042-3

upstream raw materials:

[2-((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-trimethyl-silane

(2R,3R,4R)-1,3,4-Tris-benzyloxy-6,6-bis-methylsulfanyl-hexan-2-ol

(3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde

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

Downstream raw materials:

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

3β-cholestanyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl)-α-D-glucopyranoside

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