Chloro-acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Chloro-acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester
CAS No.:189144-52-3
Molecular Formula:C₂₄H₃₅ClO₉Si
Molecular Weight:531.075
Hs Code.:

Synonyms:Chloro-acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Chloro-acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Chloro-acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

There total 7 articles about Chloro-acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-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:

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 189144-52-3
Chloro-acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) sym-collidine, 4 Angstroem molecular sieves, 2.) AgOTf, 3.) Ac₂O, pyridine / 1) CH₂Cl₂, 23 deg C, 3 h; 2) CH₂Cl₂, 0 deg C, 3 h; 3) 23 deg C, 12 h

2: 99 percent / NaOMe / methanol / 1.5 h / 50 °C

3: camphorsulfonic acid / dimethylformamide / 2 h / 23 °C

4: pyridine / 1 h / 23 °C

5: tetrafluoroboric acid / methanol; ethyl acetate / 1 h / 23 °C

6: 83 percent / pyridine / 12 h / 23 °C

With pyridine; 2,4,6-trimethyl-pyridine; tetrafluoroboric acid; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; In methanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo962300y

Reference yield:

: 39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9
1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

: 189144-52-3
Chloro-acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / α,α-dichloromethyl methyl ether, ZnCl2*Et2O / CH2Cl2 / 0.33 h / 23 °C

2: 1.) sym-collidine, 4 Angstroem molecular sieves, 2.) AgOTf, 3.) Ac₂O, pyridine / 1) CH₂Cl₂, 23 deg C, 3 h; 2) CH₂Cl₂, 0 deg C, 3 h; 3) 23 deg C, 12 h

3: 99 percent / NaOMe / methanol / 1.5 h / 50 °C

4: camphorsulfonic acid / dimethylformamide / 2 h / 23 °C

5: pyridine / 1 h / 23 °C

6: tetrafluoroboric acid / methanol; ethyl acetate / 1 h / 23 °C

7: 83 percent / pyridine / 12 h / 23 °C

With pyridine; 2,4,6-trimethyl-pyridine; tetrafluoroboric acid; zinc chloride diethyl ether; Dichloromethyl methyl ether; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo962300y

Reference yield:

: 189144-50-1
(2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,5-diol

: 189144-52-3
Chloro-acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: camphorsulfonic acid / dimethylformamide / 2 h / 23 °C

2: pyridine / 1 h / 23 °C

3: tetrafluoroboric acid / methanol; ethyl acetate / 1 h / 23 °C

4: 83 percent / pyridine / 12 h / 23 °C

With pyridine; tetrafluoroboric acid; camphor-10-sulfonic acid; In methanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo962300y