5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose

Base Information

Chemical Name:5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose
CAS No.:700870-83-3
Molecular Formula:C₂₃H₂₈O₅
Molecular Weight:384.472
Hs Code.:

Synonyms:5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose

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Chemical Property of 5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose

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Technology Process of 5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose

There total 3 articles about 5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose 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:

: (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

: 700870-83-3
5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / hydrogen / Pd/C / tetrahydrofuran / 12 h / 20 °C

2: 93 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

3: 440 mg / NaBH₄ / methanol / 12 h / 20 °C

4: 528 mg / NaH; tetrabutylammonium iodide / tetrahydrofuran / 4 h / 0 - 20 °C

With sodium tetrahydroborate; oxalyl dichloride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 2: Swern oxidation;
DOI:10.1021/jo049858n

Reference yield:

: 137585-73-0
5,6-dideoxy-1,2-O-(isopropylidene)-6-phenyl-α-D-xylo-hexofuranose

: 700870-83-3
5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

2: 440 mg / NaBH₄ / methanol / 12 h / 20 °C

3: 528 mg / NaH; tetrabutylammonium iodide / tetrahydrofuran / 4 h / 0 - 20 °C

With sodium tetrahydroborate; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1: Swern oxidation;
DOI:10.1021/jo049858n

Reference yield:

: 700870-82-2
(3aR,5R,6aS)-2,2-Dimethyl-5-phenethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one

: 700870-83-3
5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 440 mg / NaBH₄ / methanol / 12 h / 20 °C

2: 528 mg / NaH; tetrabutylammonium iodide / tetrahydrofuran / 4 h / 0 - 20 °C

With sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol;
DOI:10.1021/jo049858n