3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

Base Information

• Chemical Name: 3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose
• CAS No.: 113918-93-7
• Molecular Formula: C₂₅H₄₂O₆Si
• Molecular Weight: 466.69

Synonyms:3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

Chemical Property of 3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

There total 7 articles about 3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose 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: 87.0%

3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-methylene-α-D-ribo-hexofuranose (108470-17-3) → 3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose (113918-93-7)

Guidance literature:

With diborane; In tetrahydrofuran; at -5 ℃; for 6h;

DOI:10.1248/cpb.35.2209

Reference yield:

3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (58399-55-6) → 3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose (113918-93-7)

Guidance literature:

Multi-step reaction with 7 steps

1: LAH / tetrahydrofuran / Ambient temperature

2: NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / Ambient temperature

3: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

4: imidazole / CH₂Cl₂ / 3 h / 0 °C

5: 1.) oxalyl chloride/DMSO 2.) Et₃N / 1.) CHCl₂, -70 deg C; 2.) CH₂Cl₂, -70 to 0 deg C

6: 84 percent / n-butyllithium / tetrahydrofuran / 1.) room temp., 1 h; 2.) room temp., 3 h

7: 87 percent / B₂H₆ / tetrahydrofuran / 6 h / -5 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; diborane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1248/cpb.35.2209

Reference yield:

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside (18427-19-5) → 3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose (113918-93-7)

Guidance literature:

Multi-step reaction with 6 steps

1: NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / Ambient temperature

2: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

3: imidazole / CH₂Cl₂ / 3 h / 0 °C

4: 1.) oxalyl chloride/DMSO 2.) Et₃N / 1.) CHCl₂, -70 deg C; 2.) CH₂Cl₂, -70 to 0 deg C

5: 84 percent / n-butyllithium / tetrahydrofuran / 1.) room temp., 1 h; 2.) room temp., 3 h

6: 87 percent / B₂H₆ / tetrahydrofuran / 6 h / -5 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; diborane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1248/cpb.35.2209

upstream raw materials:

3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-methylene-α-D-ribo-hexofuranose

3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside

(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]tetrahydrofuro[2,3-d][1,3]dioxole

Downstream raw materials:

5(S)-<2(tert-butyldimethylsilyloxy)ethyl>-5,6-dihydro-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran

3-C-(2-benzyloxyethyl)-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-D-talofuranose

(2Z,4S,5S,6S)-4-(2-benzyloxyethyl)-5-hydroxy-2,6-dimethyl-7-(4-methoxybenzyloxy)hept-2-enoic acid δ-lactone

(2S,5S,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-3-methyl-5,6-dihydro-2H-pyran-2-ol

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