1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol
• CAS No.: 105938-02-1
• Molecular Formula: C₂₈H₃₀O₄
• Molecular Weight: 430.544
• Mol file: 105938-02-1.mol

Synonyms:1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol

Chemical Property of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol

There total 11 articles about 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol 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: 74.0%

tetra-O-benzyl glucopyranosyl chloride (25320-59-6) + methyllithium (917-54-4) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol (105938-02-1)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1039/CC9960002357

Reference yield: 72.0%

C30H34O4 (221183-87-5) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol (105938-02-1)

Guidance literature:

With Mo(CHCMe2Ph)2; In toluene; at 60 ℃;

DOI:10.1021/jo982331o

Reference yield: 30.0%

trimethylaluminum (75-24-1) + 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose (126709-14-6) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol (105938-02-1) + 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol (4132-32-5)

Guidance literature:

trimethylaluminum; 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose; In tetrahydrofuran; n-heptane; at 18 ℃; for 4.5h;

With water; In tetrahydrofuran; n-heptane;

DOI:10.1002/1522-2675(20000705)83:7<1542::AID-HLCA1542>3.0.CO;2-F

upstream raw materials:

benzyl bromide

tri-O-(tert-butyldimethylsilyl)-D-glucal

methyl iodide

1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol

Downstream raw materials:

(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol