(R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan

Base Information

• Chemical Name: (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan
• CAS No.: 79241-07-9
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332

Synonyms:(R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan

Chemical Property of (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan

Chemical Property:

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Technology Process of (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan

There total 11 articles about (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan 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: 97.0%

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabinohex-1-enitol (68144-11-6) + benzyl bromide (100-39-0) → (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan (79241-07-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 25 ℃;

DOI:10.1246/bcsj.75.1927

Reference yield: 67.0%

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabino-hex-1-enitol (68144-11-6,68198-85-6,86495-11-6) + benzyl bromide (100-39-0) → 1,4-anhydro-3-O-benzyl-2-deoxy-5,6-O-isopropylidene-D-arabino-hex-1-enitol (79241-07-9,79298-14-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 35 ℃; for 18h;

DOI:10.1016/0008-6215(87)80196-9

Reference yield: 61.0%

(2R,3R,4R,5R)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-O-methanesulfonyl-D-glucitol (1017236-05-3) → 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-D-ribo-hex-1-enitol (79298-14-9) + C16H20O4 (1167439-15-7) + (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan (79241-07-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; for 8h; Reflux;

DOI:10.1002/ejoc.200801226

upstream raw materials:

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabino-hex-1-enitol

benzyl bromide

(3aS,4R,6R,6aS)-4-chloro-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

D-Mannose

Downstream raw materials:

1-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-5,6-O-isopropylidne-α-D-glucofuranose

1-[(2R,3R,4S,5R)-4-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

1,4-anhydro-3-O-benzyl-2-deoxy-1,2-C-(dichloromethylene)-5,6-O-isopropylidene-D-glycero-D-glucohexitol

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