3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

Base Information

• Chemical Name: 3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose
• CAS No.: 85315-73-7
• Molecular Formula: C₁₇H₂₁IO₄
• Molecular Weight: 416.256
• Mol file: 85315-73-7.mol

Synonyms:3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

Chemical Property of 3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose

There total 1 articles about 3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose 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: 30.0%

[1-((3aR,5S,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-eth-(E)-ylidene]-hydrazine → 3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose (85315-73-7)

Guidance literature:

With iodine; triethylamine; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

DOI:10.1246/bcsj.55.3283

Reference yield:

3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose (85315-73-7) → 8,10-di-O-benzyl-3-C-(benzyloxymethyl)-3,5,7,9,11-pentadeoxy-1,2-O-isopropylidene-5,7,9,11-tetra-C-methyl-L-erythro-D-altro-β-L-talo-dodecodialdofuranose-(1,4) 12-(diethyl acetal)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 1.28 M BuLi / 1.) ether, hexane, -94 deg C to -90 deg C, 45 min, 2.) ether, hexane, -94 deg C to -90 deg C, 0.5 h

2: 31 mg / H₂, (Ph₃P)3RhCl / benzene / 14 h / 760 Torr / Ambient temperature

With Wilkinson's catalyst; n-butyllithium; hydrogen; In benzene;

DOI:10.1246/bcsj.55.3283

Reference yield:

3-C-(benzyloxymethyl)-3,5,6-trideoxy-5-iodo-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose (85315-73-7) → (3S,4S,5S,6S,7R,8R)-5,7-Bis-benzyloxy-2-((3aR,5R,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-9,9-diethoxy-4,6,8-trimethyl-nonan-3-ol

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 1.28 M BuLi / 1.) ether, hexane, -94 deg C to -90 deg C, 45 min, 2.) ether, hexane, -94 deg C to -90 deg C, 0.5 h

2: 8.4 mg / H₂, (Ph₃P)3RhCl / benzene / 14 h / 760 Torr / Ambient temperature

With Wilkinson's catalyst; n-butyllithium; hydrogen; In benzene;

DOI:10.1246/bcsj.55.3283

Downstream raw materials:

8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-D-allo-undecofuranose-(1,4)

8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4)