Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester
CAS No.:18933-64-7
Molecular Formula:C₁₄H₁₇BrO₅
Molecular Weight:345.19
Hs Code.:

Synonyms:Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

There total 1 articles about Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester 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:

: 6752-48-3,16718-95-9,18424-62-9,19877-02-2,22886-97-1,52153-29-4,52612-68-7,55331-65-2,64978-95-6,65725-24-8,66512-93-4,67968-51-8,72904-80-4,77481-69-7,131615-73-1,138663-49-7,151214-39-0
methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

: 18933-64-7
Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; 1,1,2,2-tetrachloroethane; for 2.5h; Reflux;
DOI:10.15227/orgsyn.065.0243

Reference yield: 100.0%

: 18933-64-7
Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

: 18944-96-2
methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside

Guidance literature:: With hydrogen; Raney nickel W-5; In isopropyl alcohol; for 12h; Ambient temperature;
DOI:10.1016/0008-6215(84)85014-4

Reference yield:

: 18933-64-7
Benzoic acid (2S,3S,4R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl ester

: 83532-10-9
methyl 3-(N-benzyloxycarbonylamino)-2,3,6-trideoxy-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / H₂ / Raney nickel W-5 / propan-2-ol / 12 h / Ambient temperature

2: 97 percent / triethylamine / tetrahydrofuran / 15 min, 0 deg C; 15 min, 25 deg C

3: 1.) sodium methoxide; 2.) sodium azide, ammonium chloride / 1.) MeOH, r.t., 5 h; 2.) reflux, 24 h

4: 86 percent / H₂ / PtO₂ / tetrahydrofuran / 6 h / Ambient temperature

5: 64 percent / NaHCO₃ / CH₂Cl₂ / 0.5 h / 25 °C

With sodium azide; ammonium chloride; hydrogen; sodium methylate; sodium hydrogencarbonate; triethylamine; platinum(IV) oxide; Raney nickel W-5; In tetrahydrofuran; dichloromethane; isopropyl alcohol;
DOI:10.1016/0008-6215(84)85014-4