5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

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Chemical Name:5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose
CAS No.:912567-45-4
Molecular Formula:C₄₁H₅₂O₁₁
Molecular Weight:720.857
Hs Code.:

Synonyms:5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

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Chemical Property of 5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

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Technology Process of 5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

There total 7 articles about 5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose 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: 66.0%

: 912567-58-9
3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose

: 6921-34-2
benzylmagnesium chloride

: 5-chloro-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

: 912567-45-4
5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

Guidance literature:: benzylmagnesium chloride; With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; In tetrahydrofuran; at -50 ℃; for 1h;

3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose; In tetrahydrofuran; for 2h;
DOI:10.1021/jm060310d

Reference yield: 18.0%

: 912567-43-2
1-[(3aR,5R,6R,6aR)-6-((2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-phenyl-ethanol

: 912567-45-4
5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

Guidance literature:: 1-[(3aR,5R,6R,6aR)-6-((2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-phenyl-ethanol; With dmap; phenylcarbonochloridothioate; In acetonitrile; at 20 ℃;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;
DOI:10.1021/jm060310d

Reference yield:

: 518332-41-7
2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside

: 912567-45-4
5-benzyl-5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / diethyl ether / 8 h / -78 °C

2.1: 82 percent / TBAF / tetrahydrofuran / 20 °C

3.1: tetrahydrofuran / 20 °C

4.1: PhOCSCl; DMAP / acetonitrile / 20 °C

4.2: 18 percent / Bu₃SnH; AIBN / toluene / Heating

With dmap; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; phenylcarbonochloridothioate; In tetrahydrofuran; diethyl ether; acetonitrile; 3.1: Moffatt oxidation / 5.2: Barton deoxygenation;
DOI:10.1021/jm060310d