5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose

Base Information

• Chemical Name: 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose
• CAS No.: 76801-66-6
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332
• Mol file: 76801-66-6.mol

Synonyms:5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose

Chemical Property of 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose

There total 10 articles about 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose 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: 92.0%

2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol (57575-19-6,81686-55-7) → 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose (76801-66-6)

Guidance literature:

2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol; With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 0.2h;

With triethylamine; In dichloromethane; dimethyl sulfoxide; at -78 - 20 ℃; for 1h;

DOI:10.1002/jccs.201100744

Reference yield: 88.0%

(3aR,5R,6S,6aR)-6-Benzyloxy-5-((E)-2-methoxy-vinyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole → 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose (76801-66-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 25 ℃; for 3h;

DOI:10.1016/S0040-4039(03)01870-7

Reference yield: 57.0%

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (19877-13-5) → 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranos-5-ulose (41670-98-8) + 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose (76801-66-6)

Guidance literature:

With palladium 10% on activated carbon; oxygen; copper dichloride; In tetrahydrofuran; water; Reflux;

DOI:10.1016/j.tetlet.2009.03.173

upstream raw materials:

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

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose

C₁₅H₁₈O₅

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

Downstream raw materials:

Benzyl-[2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-amine

(3aR,5R,6S,6aR)-6-Benzyloxy-5-[(4S,5S)-2,2-dimethyl-4-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-[1,3]dioxan-5-yl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

(3aR,5R,6S,6aR)-6-Benzyloxy-5-[(4R,5R)-2,2-dimethyl-4-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-[1,3]dioxan-5-yl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Acetic acid (2S,3S,4R,5S)-2-acetoxy-3-benzyloxy-5-[(R)-benzyloxy-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methyl]-tetrahydro-pyran-4-yl ester