2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose

Base Information

• Chemical Name: 2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose
• CAS No.: 221014-95-5
• Molecular Formula: C₁₉H₂₅IO₅
• Molecular Weight: 460.309

Synonyms:2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose

Chemical Property of 2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose

Chemical Property:

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Technology Process of 2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose

There total 2 articles about 2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose 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: 86.0%

(1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol (209849-12-7) → 2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose (221014-95-5)

Guidance literature:

With iodine; sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 1h;

DOI:10.1055/s-1999-3392

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose (221014-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Mg / 1.) Et₂O, reflux, 1 h, 2.) Et₂O, 1 h

2: 86 percent / I₂, NaHCO₃ / acetonitrile / 1 h / 0 °C

With iodine; sodium hydrogencarbonate; magnesium; In acetonitrile;

DOI:10.1055/s-1999-3392

Reference yield: 56.0%

2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2'-hydroxy-3'-iodopropyl)-1,2-O-isopropylidene-β-L-idofuranose (221014-95-5) → 6-C-Acetonyl-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose + Propionic acid (S)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-ylmethyl ester (221014-98-8)

Guidance literature:

With caesium carbonate; propionic acid; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1055/s-1999-3392

upstream raw materials:

(1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

Downstream raw materials:

Propionic acid (S)-5-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-tetrahydro-furan-2-ylmethyl ester

2',5-Anhydro-3-O-benzyl-6-deoxy-5-C-((2'R,S)-2',3'-dihydroxypropyl)-1,2-O-isopropylidene-β-L-idofuranose

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