.beta.-D-Glucopyranose, 1,6-anhydro-2-deoxy-2-methyl-4-O-(phenylmethyl)-

Base Information

• Chemical Name: .beta.-D-Glucopyranose, 1,6-anhydro-2-deoxy-2-methyl-4-O-(phenylmethyl)-
• CAS No.: 65190-43-4
• Molecular Formula: C14H18 O4
• Molecular Weight: 250.29
• Mol file: 65190-43-4.mol

Synonyms:6,8-Dioxabicyclo[3.2.1]octane,b-D-glucopyranose deriv.

Chemical Property of .beta.-D-Glucopyranose, 1,6-anhydro-2-deoxy-2-methyl-4-O-(phenylmethyl)-

Chemical Property:

• PSA: 47.92000
• LogP: 1.32390

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .beta.-D-Glucopyranose, 1,6-anhydro-2-deoxy-2-methyl-4-O-(phenylmethyl)-

There total 2 articles about .beta.-D-Glucopyranose, 1,6-anhydro-2-deoxy-2-methyl-4-O-(phenylmethyl)- 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%

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) + dimethylmagnesium (2999-74-8) → 4-O-benzyl-2-methyl-1,6-anhydro-β-D-glucopyranose (65190-43-4)

Guidance literature:

In diethyl ether; for 12h; Heating;

DOI:10.1016/S0040-4039(01)82944-0

Reference yield: 67.0%

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) + methyllithium (917-54-4) → (2S,3R)-1,2-dihydroxy-3-benzyloxy-6-methylheptan-4-one + 4-O-benzyl-2-methyl-1,6-anhydro-β-D-glucopyranose (65190-43-4)

Guidance literature:

methyllithium; With copper(l) iodide; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.166667h; Inert atmosphere;

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose; In tetrahydrofuran; diethyl ether; at 20 ℃; for 12h;

With ammonium chloride; In tetrahydrofuran; diethyl ether; for 1h;

DOI:10.1080/07328300802691851

Reference yield: 85.0%

acetic anhydride (108-24-7) + 4-O-benzyl-2-methyl-1,6-anhydro-β-D-glucopyranose (65190-43-4) → 4-O-benzyl-2-methyl-3-acetoxy-1,6-anhydro-β-D-glucopyranose (65190-44-5)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 2h;

DOI:10.1080/07328300802691851

upstream raw materials:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

dimethylmagnesium

methyllithium

Downstream raw materials:

(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carbaldehyde

(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid methoxy-methyl-amide