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

Base Information

• Chemical Name: methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucopyranoside
• CAS No.: 81099-73-2
• Molecular Formula: C₂₃H₃₀O₅
• Molecular Weight: 386.488
• Mol file: 81099-73-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucopyranoside 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: 59.0%

methanol (67-56-1) + 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-β-D-glucopyranose (81076-83-7) → methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-β-D-glucopyranoside (81076-84-8) + methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucopyranoside (81099-73-2)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 2h;

DOI:10.1007/BF01142802

Reference yield:

4-O-allyl-1,6-anhydro-2-deoxy-2-C-methyl-β-D-glucopyranose (91510-64-4) → methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucopyranoside (81099-73-2)

Guidance literature:

Multi-step reaction with 7 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

6: 96 percent / NaH / dimethylformamide / 1.5 h

7: 59 percent / HCl / 2 h / 20 °C

With hydrogenchloride; 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

Reference yield:

1,6-anhydro-3-O-benzyl-2,4-dideoxy-2-C-methyl-4-methylene-β-D-xylohexopyranose (81076-81-5) → methyl-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-α-D-glucopyranoside (81099-73-2)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 96 percent / NaH / dimethylformamide / 1.5 h

3: 59 percent / HCl / 2 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In N,N-dimethyl-formamide;

DOI:10.1007/BF01142802

upstream raw materials:

methanol

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

4-O-allyl-1,6-anhydro-2-deoxy-2-C-methyl-β-D-glucopyranose

benzyl bromide

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-glucoheptapyranoside

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