1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol
• CAS No.: 1169393-30-9
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332

Synonyms:1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol

Chemical Property of 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol

Chemical Property:

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Technology Process of 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol

There total 1 articles about 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol 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: 52.0%

(2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol (936946-80-4) → 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol (1169393-30-9)

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

Reference yield: 82.0%

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol (1169393-30-9) → (4S,5R)-4-(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-2-ol

Guidance literature:

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol; With mercury(II) diacetate; In tetrahydrofuran; water; at 25 ℃; for 0.5h;

With potassium iodide; In tetrahydrofuran; water; at 0 ℃; for 0.25h;

With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 ℃; for 2.5h;

DOI:10.1016/j.tet.2011.04.014

Reference yield:

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol (1169393-30-9) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → C21H25IN2O6

Guidance literature:

With N-iodo-succinimide; In dichloromethane; at -30 - 20 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.06.009

upstream raw materials:

(2S,3S,4S,5R)-1,2-O-isopropylidine-3,6-anhydro-4-O-benzyl-5-O-methane-sulfonyl-D-galactitol

Downstream raw materials:

(4S,5R)-4-(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one

(4S,5S)-4-(benzyloxy)-5-((S)-1,2-dihydroxyethyl)dihydro-furan-2(3H)-one

(4S,5S)-4-(benzyloxy)-5-vinyldihydrofuran-2(3H)-one

(4S,5S)-4-(benzyloxy)-5-((R,E)-3-hydroxy-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one

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