(2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:114729-36-1
Molecular Formula:C₂₀H₂₈O₈
Molecular Weight:396.438
Hs Code.:

Synonyms:(2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 1 articles about (2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 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:

: 124-41-4
sodium methylate

: 111833-94-4
methyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-oct-2-ulopyrano-sidono-1,5-lactone

: 114729-36-1
(2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: In methanol; chloroform; for 1h;

Reference yield: 91.0%

: 114729-36-1
(2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 74-88-4
methyl iodide

: 133634-97-6
methyl (methyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-5-O-methyl-α-D-manno-oct-2-ulopyranosid)onate

Guidance literature:: With calcium sulfate; silver(l) oxide; at 35 ℃; for 24h; the methylation was repeated three times;

Reference yield:

: 114729-36-1
(2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 133635-09-3
methyl (methyl 4-O-benzoyl-3-deoxy-5-O-methyl-α-D-manno-oct-2-ulopyranosid)onate

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / Ag₂O, CaSO₄ / 24 h / 35 °C / the methylation was repeated three times

2: 92 percent / H₂, 1percent methanolic NH₃ / 10percent Pd/C / ethyl acetate

3: 73 percent / pyridine, DMAP / 35 °C

4: 81 percent / aq. TFA, silica gel / CH₂Cl₂ / Ambient temperature

With pyridine; dmap; calcium sulfate; ammonia; hydrogen; silica gel; trifluoroacetic acid; silver(l) oxide; palladium on activated charcoal; In dichloromethane; ethyl acetate;