6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose

Base Information

Chemical Name:6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose
CAS No.:250696-91-4
Molecular Formula:C₁₄H₂₀O₅S
Molecular Weight:300.376
Hs Code.:

Synonyms:6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose

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Chemical Property of 6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose

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Technology Process of 6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose

There total 12 articles about 6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose 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: 83.0%

: 124-63-0
methanesulfonyl chloride

: 250696-90-3
(2R,3S)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-ol

: 250696-91-4
6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 6h;
DOI:10.1080/07328319908044857

Reference yield:

: 29474-73-5
(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate

: 250696-91-4
6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose

Guidance literature:: Multi-step reaction with 11 steps

1: 76 percent / 0.4 percent HCl / acetonitrile; H₂O / 8 h / 20 °C

2: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -15 - 0 °C

3: 89 percent / 1,2-dichloro-ethane / 4 h / Heating

4: 87 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

5: 78 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

6: 6.07 g / NaH / tetrahydrofuran / 20 °C

7: 64 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / -15 - 20 °C

8: 82 percent / 1,2-dichloro-ethane / 3 h / Heating

9: 88 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

10: 90 percent / CH₃ONa / methanol / 6 h / 20 °C

11: 83 percent / Et₃N / CH₂Cl₂ / 6 h / 0 °C

With 1H-imidazole; hydrogenchloride; triethylsilane; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Hydrolysis / 2: Silylation / 3: Esterification / 4: Reduction / 5: Desilylation / 6: Benzylation / 7: Reductive cleavage / 8: Esterification / 9: Reduction / 10: Deacylation / 11: Mesylation;
DOI:10.1080/07328319908044857

Reference yield:

: 31795-13-8
3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose

: 250696-91-4
6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose

Guidance literature:: Multi-step reaction with 10 steps

1: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -15 - 0 °C

2: 89 percent / 1,2-dichloro-ethane / 4 h / Heating

3: 87 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

4: 78 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

5: 6.07 g / NaH / tetrahydrofuran / 20 °C

6: 64 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / -15 - 20 °C

7: 82 percent / 1,2-dichloro-ethane / 3 h / Heating

8: 88 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

9: 90 percent / CH₃ONa / methanol / 6 h / 20 °C

10: 83 percent / Et₃N / CH₂Cl₂ / 6 h / 0 °C

With 1H-imidazole; triethylsilane; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 1: Silylation / 2: Esterification / 3: Reduction / 4: Desilylation / 5: Benzylation / 6: Reductive cleavage / 7: Esterification / 8: Reduction / 9: Deacylation / 10: Mesylation;
DOI:10.1080/07328319908044857