4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide

Base Information

Chemical Name:4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide
CAS No.:129354-11-6
Molecular Formula:C₄₃H₅₃BrO₆Si₂
Molecular Weight:801.965
Hs Code.:

Synonyms:4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide

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Technology Process of 4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide

There total 9 articles about 4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-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:

: 129354-33-2
4-Nitro-benzoic acid (3S,4S,5R,6R)-5-acetoxy-3-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl ester

: 129354-11-6
4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide

Guidance literature:: With hydrogen bromide; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1016/0008-6215(90)84222-G

Reference yield:

: 128376-94-3
2,2,2-trichloroethyl 4,6-O-isopropylidene-α-D-mannopyranoside

: 129354-11-6
4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide

Guidance literature:: Multi-step reaction with 8 steps

1: 71 percent / imidazole / dimethylformamide / 48 h

2: 45 percent / KH, Bu₄NI / dimethylformamide / 16 h / 20 °C

3: 96 percent / 70percent aq. AcOH / 1 h / 70 °C

4: imidazole / dimethylformamide / 24 h / 20 °C

5: 82 percent / pyridine / 16 h / 20 °C

6: 60 percent / Zn, AcOH / tetrahydrofuran / 1.) 16 h, 20 deg C 2.) 15 h, 20 deg C

7: 83 percent / pyridine / 20 h / 20 °C

8: HBr / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; 1H-imidazole; hydrogen bromide; tetra-(n-butyl)ammonium iodide; potassium hydride; acetic acid; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(90)84222-G

Reference yield:

: 129354-05-8
2,2,2-trichloroethyl 3-O-tert-butyldiphenylsilyl-4,6-O-isopropylidene-α-D-mannopyranoside

: 129354-11-6
4-O-acetyl-2-O-allyl-3,6-di-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl bromide

Guidance literature:: Multi-step reaction with 7 steps

1: 45 percent / KH, Bu₄NI / dimethylformamide / 16 h / 20 °C

2: 96 percent / 70percent aq. AcOH / 1 h / 70 °C

3: imidazole / dimethylformamide / 24 h / 20 °C

4: 82 percent / pyridine / 16 h / 20 °C

5: 60 percent / Zn, AcOH / tetrahydrofuran / 1.) 16 h, 20 deg C 2.) 15 h, 20 deg C

6: 83 percent / pyridine / 20 h / 20 °C

7: HBr / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; 1H-imidazole; hydrogen bromide; tetra-(n-butyl)ammonium iodide; potassium hydride; acetic acid; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(90)84222-G