1,6-Anhydro-2-deoxy-2-methyl-4-C-methyl-3-O-(phenylmethyl)-beta-D-glucopyranose

Base Information

• Chemical Name: 1,6-Anhydro-2-deoxy-2-methyl-4-C-methyl-3-O-(phenylmethyl)-beta-D-glucopyranose
• CAS No.: 81099-75-4
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• DSSTox Substance ID: DTXSID101141482
• Mol file: 81099-75-4.mol

Synonyms:DTXSID101141482;1,6-Anhydro-2-deoxy-2-methyl-4-C-methyl-3-O-(phenylmethyl)-beta-D-glucopyranose;81099-75-4

Chemical Property of 1,6-Anhydro-2-deoxy-2-methyl-4-C-methyl-3-O-(phenylmethyl)-beta-D-glucopyranose

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 315

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(C2COC1O2)(C)O)OCC3=CC=CC=C3
• Isomeric SMILES: C[C@@H]1[C@H]([C@]([C@H]2CO[C@@H]1O2)(C)O)OCC3=CC=CC=C3

Technology Process of 1,6-Anhydro-2-deoxy-2-methyl-4-C-methyl-3-O-(phenylmethyl)-beta-D-glucopyranose

There total 24 articles about 1,6-Anhydro-2-deoxy-2-methyl-4-C-methyl-3-O-(phenylmethyl)-beta-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: 98.5%

1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-4-O-mesyl-β-D-glucopyranose (81076-82-6) → 1,6-anhydro-3-O-benzyl-2-desoxy-2,4-di-C-methyl-β-D-glucopyranose (81099-75-4)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/S0040-4039(01)82945-2

Reference yield: 56.0%

C15H18O4 (97321-52-3,97321-53-4,97321-55-6,98329-45-4) → 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose (81076-77-9) + 1,6-anhydro-3-O-benzyl-2-desoxy-2,4-di-C-methyl-β-D-glucopyranose (81099-75-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.166667h; Yields of byproduct given;

DOI:10.1016/0008-6215(85)85189-2

Reference yield:

1,6-anhydro-3-O-benzyl-2,4-dideoxy-2-C-methyl-4-methylene-β-D-xylohexopyranose (81076-81-5) → 1,6-anhydro-3-O-benzyl-2-desoxy-2,4-di-C-methyl-β-D-glucopyranose (81099-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: m-chloroperoxybenzoic acid / CHCl₃ / 1 h / Heating

2: 56 percent / lithium aluminum hydride / tetrahydrofuran / 0.17 h

With lithium aluminium tetrahydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform;

DOI:10.1016/0008-6215(85)85189-2

upstream raw materials:

1,6-anhydro-3-O-benzyl-2,4-dideoxy-2-C-methyl-4-methylene-β-D-xylohexopyranose

C₁₅H₁₈O₄

C₁₅H₁₈O₄

1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-4-O-mesyl-β-D-glucopyranose

Downstream raw materials:

methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-6-aldo-α-D-glucopyranoside

methyl-2,6,7-tridesoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucohept-6-enopyranoside

methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucopyranoside

methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-β-D-glucopyranoside