(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole

Base Information

• Chemical Name: (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole
• CAS No.: 133004-71-4
• Molecular Formula: C₂₉H₃₁NO₅
• Molecular Weight: 473.569

Synonyms:(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole

Chemical Property of (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole

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Technology Process of (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole

There total 4 articles about (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole 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: 80.0%

N-(3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-mannopyranosyl)acetamide → (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole (133004-71-4) + 2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline (65372-02-3)

Guidance literature:

With water; silver trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 12h; stereoselective reaction;

DOI:10.1002/ejoc.201500001

Reference yield: 65.0%

3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) + acetonitrile (75-05-8,26809-02-9) → (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole (133004-71-4)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; for 2h;

DOI:10.1002/chem.19970030614

Reference yield: 37.0%

acetonitrile (75-05-8,26809-02-9) + p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside (131531-76-5) → (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-<(benzyloxy)-methyl>-2-methyl-5H-pyrano<2,3-d>oxazole (133004-71-4)

Guidance literature:

acetonitrile; p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside; With N-iodo-succinimide; trifluoromethylsulfonic anhydride; at -25 ℃; Inert atmosphere;

With triethylamine; In acetonitrile;

DOI:10.1002/chem.201100732

upstream raw materials:

3,4,6-tri-O-benzyl-D-glucal epoxide

acetonitrile

p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside

3,4,6-tri-O-benzyl-D-glucal

Downstream raw materials:

Acetic acid (2R,3R,4S,5S,6S)-6-((2R,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-4,5-bis-benzyloxy-2-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester

N-<1-benzyl N-(tert-butyloxycarbonyl)-4-L-aspartyl>-2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine

2-O-Acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine

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