4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose

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Chemical Name:4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose
CAS No.:153946-35-1
Molecular Formula:C₁₅H₂₇NO₉
Molecular Weight:365.381
Hs Code.:

Synonyms:4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose

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Chemical Property of 4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose

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Technology Process of 4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose

There total 8 articles about 4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose 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: 73.0%

: 153946-34-0
4-acetamido-1,6-di-O-acetyl-2,4-dideoxy-3-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose

: 153946-35-1
4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose

Guidance literature:: With IRA-400 (OH) resin; In methanol;
DOI:10.1016/S0040-4039(00)61476-4

Reference yield:

: 104629-48-3
(1R,2R,3S)-5-oxo-3-<(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy>cyclohexane-1,2-dicarboxylic anhydride

: 153946-35-1
4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / NaCNBH₃ / acetic acid

2: (COCl)2 / dimethylformamide; CH₂Cl₂

3: NaN₃ / tetrahydrofuran

4: 98 percent / benzene / 2 h / Heating

5: 35 percent / NEt₃, water / tetrahydrofuran

6: 1.) LiAlH₄; 2.) pyridine / 1.) THF, reflux; 2.) DMAP

7: 73 percent / IRA-400 (OH) resin / methanol

With pyridine; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; IRA-400 (OH) resin; water; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)61476-4

Reference yield:

: 104629-46-1
(1R,2R,3S)-3-<(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy>-8-trimethylsilyloxycyclohex-4-ene-1,2-dicarboxylic anhydride

: 153946-35-1
4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose

Guidance literature:: Multi-step reaction with 8 steps

1: concd. HCl / CHCl₃

2: 70 percent / NaCNBH₃ / acetic acid

3: (COCl)2 / dimethylformamide; CH₂Cl₂

4: NaN₃ / tetrahydrofuran

5: 98 percent / benzene / 2 h / Heating

6: 35 percent / NEt₃, water / tetrahydrofuran

7: 1.) LiAlH₄; 2.) pyridine / 1.) THF, reflux; 2.) DMAP

8: 73 percent / IRA-400 (OH) resin / methanol

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; IRA-400 (OH) resin; water; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)61476-4