(2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan

Base Information

• Chemical Name: (2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan
• CAS No.: 492470-85-6
• Molecular Formula: C₂₀H₂₃NO₆
• Molecular Weight: 373.406

Synonyms:(2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan

Chemical Property of (2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan

There total 2 articles about (2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan 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: 68.0%

(2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-iodomethyl-5-methoxy-tetrahydro-furan (492470-86-7) → (2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan (492470-85-6)

Guidance literature:

With 3,5-dihydroxyphenol; sodium nitrite; In dimethyl sulfoxide; at 20 ℃; for 72h;

DOI:10.1016/S0040-4039(02)01760-4

Reference yield:

methyl 2,3-di-O-benzyl-α-D-arabinofuranoside (16896-03-0,16896-04-1,30589-89-0,53496-31-4,70831-62-8,103476-40-0,128821-26-1) → (2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan (492470-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / Heating

2: 68 percent / NaNO₂; phloroglucinol*H₂O / dimethylsulfoxide / 72 h / 20 °C

With 1H-imidazole; 3,5-dihydroxyphenol; iodine; triphenylphosphine; sodium nitrite; In dimethyl sulfoxide; toluene;

DOI:10.1016/S0040-4039(02)01760-4

Reference yield: 48.0%

2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose (94273-27-5) + (2S,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-furan (492470-85-6) → 1-((2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-((2R,3R,4S,5S)-3,4-bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-nitro-ethanol (492470-84-5)

Guidance literature:

With potassium fluoride; 18-crown-6 ether; In acetonitrile; at 20 ℃; for 3.5h;

DOI:10.1016/S0040-4039(02)01760-4

upstream raw materials:

(2S,3S,4S,5S)-3,4-Bis-benzyloxy-2-iodomethyl-5-methoxy-tetrahydro-furan

methyl 2,3-di-O-benzyl-α-D-arabinofuranoside

Downstream raw materials:

1-((2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-((2R,3R,4S,5S)-3,4-bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-nitro-ethanol

methyl 2,3-di-O-benzyl-6-C-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-5,6-dideoxy-α-D-arabino-hexofuranoside

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