Methyl 3-O-benzyl-2-deoxy-alpha-D-arabino-hexopyranoside

Base Information

• Chemical Name: Methyl 3-O-benzyl-2-deoxy-alpha-D-arabino-hexopyranoside
• CAS No.: 119874-56-5
• Molecular Formula: C₁₄H₂₀O₅
• Molecular Weight: 268.31
• DSSTox Substance ID: DTXSID301184905
• Nikkaji Number: J1.583.915E
• Mol file: 119874-56-5.mol

Synonyms:SCHEMBL1776371;DTXSID301184905;Methyl 3-O-benzyl-2-deoxy-alpha-D-arabino-hexopyranoside;Methyl 2-deoxy-3-O-(phenylmethyl)-alpha-D-arabino-hexopyranoside;119874-56-5

Chemical Property of Methyl 3-O-benzyl-2-deoxy-alpha-D-arabino-hexopyranoside

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 268.13107373
• Heavy Atom Count: 19
• Complexity: 254

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1CC(C(C(O1)CO)O)OCC2=CC=CC=C2
• Isomeric SMILES: CO[C@@H]1C[C@H]([C@@H]([C@H](O1)CO)O)OCC2=CC=CC=C2

Technology Process of Methyl 3-O-benzyl-2-deoxy-alpha-D-arabino-hexopyranoside

There total 24 articles about Methyl 3-O-benzyl-2-deoxy-alpha-D-arabino-hexopyranoside 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: 87.0%

(4aR,6S,8R,8aS)-8-Benzyloxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine → (2R,3S,4R,6S)-4-(benzyloxy)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3-ol (119874-56-5)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 45 ℃;

DOI:10.1021/ol0617401

Reference yield: 80.5%

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside (63592-79-0) → (2R,3S,4S)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ol (3868-11-9,64951-98-0,106444-93-3,119874-56-5,151130-22-2)

Guidance literature:

With methanol; toluene-4-sulfonic acid; In chloroform; for 3h; Heating;

DOI:10.1139/v86-296

Reference yield: 79.0%

(4aR,6S,8R,8aS)-8-(benzyloxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine (80667-89-6) → (2R,3S,4R,6S)-4-(benzyloxy)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3-ol (119874-56-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 12h;

DOI:10.1055/s-2006-950325

upstream raw materials:

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside

Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside

methanol

3-O-benzyl-2-deoxy-β-D-arabino-hexopyranose

Downstream raw materials:

(2R,4R,6S)-4-Benzyloxy-6-methoxy-2-methyl-dihydro-pyran-3-one

Methyl 3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside

methyl 2,6-dideoxy-3-O-benzyl-α-D-lyxo-hexopyranoside

methyl 3-O-benzyl-2,4-dideoxy-α-pent-4-enopyranoside