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

Base Information

• Chemical Name: 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose
• CAS No.: 81076-77-9
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 81076-77-9.mol

Synonyms:1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose

Chemical Property of 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose

There total 12 articles about 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose 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%

methylmagnesium bromide (75-16-1) + 1,6-anhydro-2-desoxy-2-C-methyl-3-O-benzyl-β-D-xylohexapyranos-4-ylose (91510-66-6,97321-50-1) → 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose (81076-77-9)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)90023-1

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:

4-O-allyl-1,6-anhydro-2-deoxy-2-C-methyl-β-D-glucopyranose (91510-64-4) → 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose (81076-77-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / NaH / dimethylformamide / 1.5 h / 20 °C

2: 1.) t-BuOK, 2.) HgO, HgCl₂ / 1.) DMSO, 100 deg C, 1 h, 2.) acetone, water

3: 98 percent / DMSO, (COCl)2 / CH₂Cl₂ / 0.42 h / -60 °C

4: 84 percent / n-BuLi / hexane; benzene / 1.) 15 min, 2.) reflux, 10 min

5: 1.) m-CPBA, 2.) LiAlH₄ / 1.) CHCl₃, reflux, 12 h, 2.) THF

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; potassium tert-butylate; sodium hydride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; mercury dichloride; mercury(II) oxide; In hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1007/BF01142802

upstream raw materials:

methylmagnesium bromide

1,6-anhydro-2-desoxy-2-C-methyl-3-O-benzyl-β-D-xylohexapyranos-4-ylose

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

C₁₅H₁₈O₄

Downstream raw materials:

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

1,6-anhydro-2,4-didesoxy-2,4-di-C-methyl-3-O-benzyl-β-D-galactopyranose

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

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