1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose

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Chemical Name:1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose
CAS No.:76498-56-1
Molecular Formula:C₁₄H₂₄O₆
Molecular Weight:288.341
Hs Code.:

Synonyms:1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose

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Chemical Property of 1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose

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Technology Process of 1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose

There total 2 articles about 1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose 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: 47.0%

: 32786-02-0
2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde

: 925-90-6
ethylmagnesium bromide

: 20880-92-6
2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

: 76498-56-1
1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose

Guidance literature:: In diethyl ether; at -78 ℃; for 2h; Yields of byproduct given;
DOI:10.1016/S0957-4166(99)00035-X

Reference yield: 4.0%

: 32786-02-0
2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde

: 925-90-6
ethylmagnesium bromide

: 20880-92-6
2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

: 76498-56-1
1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose

: (S)-1-((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-propan-1-ol

Guidance literature:: In diethyl ether; at 35 ℃; for 2h; Yields of byproduct given;
DOI:10.1016/S0957-4166(99)00035-X

Reference yield:

: 76498-56-1
1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose

: 72519-59-6
(2R,3R)-3-Hydroxy-2-methyl-3-phenyl-1-((3aR,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-propan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / 1.) N-chlorosuccinimide, dimethylsulfide / CH₂Cl₂ / 1.) 0 deg C, 2.) -25 deg C, 2.75 h

2: 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, 0 deg C, 10 min, 2.) -70 deg C, 30 min, 3) -70 deg C, 5 min

With N-chloro-succinimide; n-butyllithium; dimethylsulfide; diisopropylamine; In dichloromethane;
DOI:10.1021/jo00320a014