benzyl 2-O-benzyl-4,6-dideoxy-3-O-methyl-L-xylohexopyranoside

Base Information

• Chemical Name: benzyl 2-O-benzyl-4,6-dideoxy-3-O-methyl-L-xylohexopyranoside
• CAS No.: 111304-09-7
• Molecular Formula: C₂₁H₂₆O₄
• Molecular Weight: 342.435
• Mol file: 111304-09-7.mol

Synonyms:

Chemical Property of benzyl 2-O-benzyl-4,6-dideoxy-3-O-methyl-L-xylohexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-O-benzyl-4,6-dideoxy-3-O-methyl-L-xylohexopyranoside

There total 14 articles about benzyl 2-O-benzyl-4,6-dideoxy-3-O-methyl-L-xylohexopyranoside 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: 83.0%

(3S,4R,6S)-2,3-Bis-benzyloxy-6-methyl-tetrahydro-pyran-4-ol (111304-07-5,111304-08-6,111304-13-3,111304-14-4) + methyl iodide (74-88-4) → benzyl 2-O-benzyl-4,6-dideoxy-3-O-methyl-L-xylohexopyranoside (111304-09-7,111304-15-5,111304-16-6,111551-08-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

Reference yield: 83.0%

(3R,4S,6R)-2,3-Bis-benzyloxy-6-methyl-tetrahydro-pyran-4-ol (111304-07-5,111304-08-6,111304-13-3,111304-14-4) + methyl iodide (74-88-4) → (3R,4S,6R)-2,3-Bis-benzyloxy-4-methoxy-6-methyl-tetrahydro-pyran (111304-09-7,111304-15-5,111304-16-6,111551-08-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

Reference yield:

dl-2,6-octadiene-4,5-diolhexanediene-3,4-diol (4486-59-3,19700-06-2,19700-98-2,26171-87-9,99944-93-1,102517-71-5,114612-51-0) → (3R,4S,6R)-2,3-Bis-benzyloxy-4-methoxy-6-methyl-tetrahydro-pyran (111304-09-7,111304-15-5,111304-16-6,111551-08-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 46 percent / BaO/Ba(OH)2 / dimethylformamide

2: 35 percent / (-)-diethyltartrate, Ti(OiPr)4, tBuOOH / CH₂Cl₂

3: 86 percent / sodiumhydridobis(2-methoxyethoxy)aluminate / tetrahydrofuran

4: 1) O₃, 2) Me₂S / 1) MeOH/CH₂Cl₂

5: 70 percent / HCl

6: 83 percent / NaH / dimethylformamide

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; barium dihydroxide; dimethylsulfide; sodium hydride; ozone; (-)-diethyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride; barium(II) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(3R,4S,6R)-2,3-Bis-benzyloxy-6-methyl-tetrahydro-pyran-4-ol

methyl iodide

dl-2,6-octadiene-4,5-diolhexanediene-3,4-diol

benzyl bromide

Downstream raw materials:

L-chalcose

Refernces

• 1、 Kuefner, Ulrike,Schmidt, Richard R.. "Divinylglykole zur Synthese von Desoxyhexosen - Synthese von D- und L-Chalcose". . p. 90 - 91. Retrieved 2007/10/02.