4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide

Base Information

Chemical Name:4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide
CAS No.:205869-82-5
Molecular Formula:C₂₇H₂₃BrO₇
Molecular Weight:539.379
Hs Code.:

Synonyms:4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide

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Chemical Property of 4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide

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Technology Process of 4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide

There total 6 articles about 4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide 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: 96.0%

: 205869-83-6
1,5-anhydro-2,4,6-tri-O-benzoyl-3-O-benzyl-D-arabino-hex-1-enitol

: 205869-82-5
4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide

Guidance literature:: With N-Bromosuccinimide; ethanol; 4 A molecular sieve; In dichloromethane; for 0.5h;
DOI:10.1016/S0008-6215(97)00249-8

Reference yield:

: 582-52-5
1,2:5,6-diacetone-D-glucose

: 205869-82-5
4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH, tetrabutylammonium iodide / 1.) THF, 0 deg C -> room temperature, 2.) THF, 50 deg C, 2 h

2: 81 percent / Dowex 50 (H⁽¹⁺⁾) / H₂O / 2 h / 70 °C

3: 23.2 g / pyridine / CHCl₃ / 24 h / Ambient temperature

4: hydrogen bromide, acetic acid / CH₂Cl₂ / 0.17 h

5: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH₂Cl₂ / 0.5 h

With pyridine; N-Bromosuccinimide; ethanol; 4 A molecular sieve; Dowex 50 (H⁽¹⁺⁾); hydrogen bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; chloroform; water;
DOI:10.1016/S0008-6215(97)00249-8

Reference yield:

: 101475-83-6
3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

: 205869-82-5
4,6-di-O-benzoyl-3-O-benzyl-1-thio-α-D-arabino-hexopyranosid-2-ulosyl bromide

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / Dowex 50 (H⁽¹⁺⁾) / H₂O / 2 h / 70 °C

2: 23.2 g / pyridine / CHCl₃ / 24 h / Ambient temperature

3: hydrogen bromide, acetic acid / CH₂Cl₂ / 0.17 h

4: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH₂Cl₂ / 0.5 h

With pyridine; N-Bromosuccinimide; ethanol; 4 A molecular sieve; Dowex 50 (H⁽¹⁺⁾); hydrogen bromide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; chloroform; water;
DOI:10.1016/S0008-6215(97)00249-8