1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

Base Information

Chemical Name:1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose
CAS No.:331633-97-7
Molecular Formula:C₂₀H₁₉N₅O₈S
Molecular Weight:489.466
Hs Code.:

Synonyms:1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

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Chemical Property of 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

There total 9 articles about 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose 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: 65.0%

: 70-34-8,65727-75-5
2,4-Dinitrofluorobenzene

: 331633-94-4
1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose

: 1,6-anhydro-3-azido-3-deoxy-2-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-2-thio-β-D-idopyranose

: 331633-97-7
1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

Guidance literature:: 1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose; With mercury(II) diacetate; tetrabutylammoniun azide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;

2,4-Dinitrofluorobenzene; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 18h; Further stages.;
DOI:10.1021/ja003713q

Reference yield:

: 58394-32-4,52630-80-5,52630-81-6
1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose

: 331633-97-7
1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH; TBAI / dimethylformamide / 0.17 h / 0 °C

1.2: 62 percent / dimethylformamide / 12 h / 20 °C

2.1: 90 percent / aq. OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 3 h / 0 °C

3.1: SOCl₂; Et₃N / CH₂Cl₂ / 0 °C

3.2: 66 percent / aq.NaIO₄; RuCl₃ / CCl₄; acetonitrile / 0.25 h / 20 °C

4.1: KSAc / dimethylformamide / 2 h / 60 °C

4.2: 91 percent / NaOMe / methanol / 0.5 h / 20 °C

5.1: TBAN₃; Hg(OAc)2 / dimethylformamide / 24 h / 0 - 20 °C

5.2: 65 percent / DIEA / CH₂Cl₂ / 18 h / 20 °C

With osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; mercury(II) diacetate; tetrabutylammoniun azide; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; potassium thioacetate; In dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/ja003713q

Reference yield:

: 58394-31-3,52630-80-5,52630-81-6
1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose

: 331633-97-7
1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

Guidance literature:: Multi-step reaction with 7 steps

1.1: NMO; TPAP; 4A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

2.1: CeCl₃; NaBH₄ / CH₂Cl₂; methanol / 1 h / -78 °C

3.1: NaH; TBAI / dimethylformamide / 0.17 h / 0 °C

3.2: 62 percent / dimethylformamide / 12 h / 20 °C

4.1: 90 percent / aq. OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 3 h / 0 °C

5.1: SOCl₂; Et₃N / CH₂Cl₂ / 0 °C

5.2: 66 percent / aq.NaIO₄; RuCl₃ / CCl₄; acetonitrile / 0.25 h / 20 °C

6.1: KSAc / dimethylformamide / 2 h / 60 °C

6.2: 91 percent / NaOMe / methanol / 0.5 h / 20 °C

7.1: TBAN₃; Hg(OAc)2 / dimethylformamide / 24 h / 0 - 20 °C

7.2: 65 percent / DIEA / CH₂Cl₂ / 18 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; mercury(II) diacetate; tetrabutylammoniun azide; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; potassium thioacetate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/ja003713q