(2R,3R,3aR,5S,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]furan

Base Information

• Chemical Name: (2R,3R,3aR,5S,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]furan
• CAS No.: 326487-10-9
• Molecular Formula: C₂₂H₂₅IO₄
• Molecular Weight: 480.343

Synonyms:(2R,3R,3aR,5S,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]furan

Chemical Property of (2R,3R,3aR,5S,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]furan

Chemical Property:

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Technology Process of (2R,3R,3aR,5S,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]furan

There total 2 articles about (2R,3R,3aR,5S,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]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:

1-(2',3',5'-tri-O-benzyl-D-arabinofuranosyl)prop-2-ene → (2R,3R,3aR,5S,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]furan (326487-10-9) + (2R,3R,3aR,5R,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]furan

Guidance literature:

With iodine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1039/b006192l

Reference yield:

1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose (62255-44-1) → (2R,3R,3aR,5S,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]furan (326487-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / BF₃*OEt₂ / acetonitrile / 20 °C

2: I₂ / CH₂Cl₂ / 12 h / 0 °C

With boron trifluoride diethyl etherate; iodine; In dichloromethane; acetonitrile; 1: Alkylation / 2: Cyclization;

DOI:10.1039/b006192l

Reference yield: 87.0%

(2R,3R,3aR,5S,6aS)-3-Benzyloxy-2-benzyloxymethyl-5-iodomethyl-hexahydro-furo[3,2-b]furan (326487-10-9) → (2S,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan (326487-12-1)

Guidance literature:

With tetrabutylammoniun azide; In toluene; at 60 ℃; for 24h;

DOI:10.1039/b006192l

upstream raw materials:

1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose

Downstream raw materials:

(2S,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

(2S,4aS,5R,6R,6aR)-2-azidomethyl-6-benzyloxy-5-(hydroxymethyl)hexahydrofuro[3,2-b]furan

(2S,4aS,5R,6R,6aR)-2-azidomethyl-6-benzyloxy-5-carboxylhexahydrofuro[3,2-b]furan

(2S,4aS,5R,6R,6aR)-2-azidomethyl-6-benzyloxy-5-(acetoxymethyl)hexahydrofuro[3,2-b]furan

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