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

Base Information

• Chemical Name: 3-C-benzyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-L-talofuranose
• CAS No.: 98039-22-6
• Molecular Formula: C₂₆H₃₄O₆
• Molecular Weight: 442.552
• Mol file: 98039-22-6.mol

Synonyms:3-C-benzyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-L-talofuranose

Chemical Property of 3-C-benzyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-L-talofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-C-benzyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-L-talofuranose

There total 10 articles about 3-C-benzyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-L-talofuranose 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:

3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose (98039-21-5) → 3-C-benzyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-α-D-allofuranose (98039-23-7) + 3-C-benzyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-L-talofuranose (98039-22-6)

Guidance literature:

With hydrogen; rhodium on alumina; In ethanol; at 0 ℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1039/P19850000019

Reference yield:

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol (69832-48-0) → 3-C-benzyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-L-talofuranose (98039-22-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 76.2 percent / NaH, DMSO / 1 h / Ambient temperature

2: 94.5 percent / 2 percent H₂SO₄ / methanol / 15 h / Ambient temperature

3: pyridine / Ambient temperature

4: 60 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

5: 67 percent / tetrahydrofuran; dimethylsulfoxide / 4.5 h / Ambient temperature

6: 85 percent / PCC, molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / Ambient temperature

7: 77 percent / tetrahydrofuran / 8 h / Ambient temperature

8: H₂ / 5 percent Rh-Al₂O₃ / ethanol / 2 h / 0 °C

With 4 A molecular sieve; sulfuric acid; hydrogen; sodium hydride; potassium carbonate; dimethyl sulfoxide; pyridinium chlorochromate; rhodium on alumina; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1039/P19850000019

Reference yield:

3-C-benzyloxymethyl-3-deoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-α-D-ribo-hexofuranos-5-ulose (98039-29-3) → 3-C-benzyloxymethyl-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-L-talofuranose (98039-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / tetrahydrofuran / 8 h / Ambient temperature

2: H₂ / 5 percent Rh-Al₂O₃ / ethanol / 2 h / 0 °C

With hydrogen; rhodium on alumina; In tetrahydrofuran; ethanol;

DOI:10.1039/P19850000019

upstream raw materials:

3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

4-methoxybenzyl alcohol sodium salt

benzyl chloride

Downstream raw materials:

(2R,3R,4S)-2-benzyloxymethyl-3-formyloxy-5-(4-methoxybenzyloxy)-4-methylpentanal

(2R,3R,4R)-2-benzyloxymethyl-3-formyloxy-5-(4-methoxybenzyloxy)-4-methylpentanal

(2S,3R,4S,5R)-4-Benzyloxymethyl-5-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol