methyl (1S,2R,3R,5R)-5-hydroxy-2-nitro-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate

Base Information

• Chemical Name: methyl (1S,2R,3R,5R)-5-hydroxy-2-nitro-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate
• CAS No.: 844477-41-4
• Molecular Formula: C₂₂H₃₁NO₁₅
• Molecular Weight: 549.486

Synonyms:methyl (1S,2R,3R,5R)-5-hydroxy-2-nitro-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate

Chemical Property of methyl (1S,2R,3R,5R)-5-hydroxy-2-nitro-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate

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Technology Process of methyl (1S,2R,3R,5R)-5-hydroxy-2-nitro-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate

There total 2 articles about methyl (1S,2R,3R,5R)-5-hydroxy-2-nitro-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate 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: 73.0%

methyl (1S,2R,3R)-2-nitro-5-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate (844477-37-8) → methyl (1S,2R,3R,5R)-5-hydroxy-2-nitro-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate (844477-41-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 6h; cooling;

DOI:10.1039/b410556g

Reference yield:

6-Nitro-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-3-trimethylsilanyloxy-cyclohex-3-enecarboxylic acid methyl ester → methyl (1S,2R,3R,5R)-5-hydroxy-2-nitro-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate (844477-41-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.040 g / aq. AcOH / 2 h

2: 73 percent / NaBH₄ / methanol / 6 h / cooling

With sodium tetrahydroborate; acetic acid; In methanol;

DOI:10.1039/b410556g

Reference yield:

methyl (1S,2R,3R,5R)-5-hydroxy-2-nitro-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate (844477-41-4) → (1S,2R,3R,5R)-2-Amino-5-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexanecarboxylic acid methyl ester

Guidance literature:

With aluminium amalgam; In methanol; for 4h;

DOI:10.1039/b410556g

upstream raw materials:

methyl (1S,2R,3R)-2-nitro-5-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-cyclohexane-1-carboxylate

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