4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranosyl bromide

Base Information

Chemical Name:4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranosyl bromide
CAS No.:173207-87-9
Molecular Formula:C₃₁H₃₇BrO₁₇
Molecular Weight:761.529
Hs Code.:

Synonyms:4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranosyl bromide

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Chemical Property of 4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranosyl bromide

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Technology Process of 4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranosyl bromide

There total 8 articles about 4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranosyl 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: 93.0%

: 173207-86-8
phenyl 4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

: Benzoic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-bromo-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

: 173207-87-9
4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranosyl bromide

Guidance literature:: With 3 A molecular sieve; bromine; In dichloromethane; for 5.5h; Yields of byproduct given; Ambient temperature;

Reference yield:

: 22860-22-6
2,3,4,6-tetra-O-acetyl-α-D-mannopyranose

: 173207-87-9
4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranosyl bromide

Guidance literature:: Multi-step reaction with 5 steps

1: 97.5 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1) -20 deg C, 1 h; 2) 0 deg C, 2 h

2: 91 percent / molecular sieves (3 Angstroem), trimethylsilyl triflate / CH₂Cl₂ / 0.58 h / -30 - -25 °C

3: aq. AcOH / 1.5 h / 60 - 65 °C

4: pyridine / 4 °C

5: 93 percent / Br₂, molecular sieves (3 Angstroem) / CH₂Cl₂ / 5.5 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; bromine; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

Reference yield:

: 121238-27-5
2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

: 173207-87-9
4,6-di-O-acetyl-2-O-benzoyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1-thio-α-D-mannopyranosyl bromide

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / molecular sieves (3 Angstroem), trimethylsilyl triflate / CH₂Cl₂ / 0.58 h / -30 - -25 °C

2: aq. AcOH / 1.5 h / 60 - 65 °C

3: pyridine / 4 °C

4: 93 percent / Br₂, molecular sieves (3 Angstroem) / CH₂Cl₂ / 5.5 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; bromine; acetic acid; In dichloromethane;