methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-phenylethyl)-α-D-altropyranoside

Base Information

Chemical Name:methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-phenylethyl)-α-D-altropyranoside
CAS No.:661467-06-7
Molecular Formula:C₂₂H₂₆O₅
Molecular Weight:370.445
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-phenylethyl)-α-D-altropyranoside

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Chemical Property of methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-phenylethyl)-α-D-altropyranoside

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Technology Process of methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-phenylethyl)-α-D-altropyranoside

There total 1 articles about methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-phenylethyl)-α-D-altropyranoside 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: 58.0%

: 622-24-2
2-phenylethyl chloride

: 3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2,2880-96-8
methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside

: 661467-06-7
methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-phenylethyl)-α-D-altropyranoside

Guidance literature:: 2-phenylethyl chloride; With iodine; magnesium; In tetrahydrofuran; toluene; at 70 ℃;

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside; In tetrahydrofuran; toluene; at 110 ℃; for 1h;

Reference yield: 85.0%

: 661467-06-7
methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-phenylethyl)-α-D-altropyranoside

: 871917-08-7
methyl 4-O-benzoyl-6-bromo-3,6-dideoxy-3-(2-phenylethyl)-α-D-altropyranoside

Guidance literature:: With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 0.666667h; Heating;
DOI:10.1016/j.tet.2005.08.116

Reference yield:

: 661467-06-7
methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-phenylethyl)-α-D-altropyranoside

: 1α,25-dihydroxy-2α-(2-phenylethyl)vitamin D₃

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / N-bromosuccinimide; BaCO₃ / CCl₄ / 0.67 h / Heating

2.1: 57 percent / zinc; sodium cyanoborohydride / H₂O; propan-1-ol / 0.83 h / 95 °C

3.1: 88 percent / triethylamine; N,N-dimethylpyridin-4-amine / CH₂Cl₂ / 4 h / 20 °C

4.1: 82 percent / LiHMDS / tetrahydrofuran; hexane / 1.08 h / -78 - 20 °C

5.1: BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

5.2: 80 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 2 h / -78 °C

6.1: K₂CO₃ / methanol / 4.5 h / 20 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 0.67 h / 0 °C

8.1: triethylamine / [Pd(PPh₃)4] / toluene / 2 h / Heating

9.1: TBAF / tetrahydrofuran / 48.5 h / 20 - 60 °C

With 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; sodium cyanoborohydride; potassium carbonate; triethylamine; barium carbonate; lithium hexamethyldisilazane; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; propan-1-ol; tetrachloromethane; hexane; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2005.08.116