Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester
CAS No.:189144-53-4
Molecular Formula:C₂₂H₃₄O₈Si
Molecular Weight:454.593
Hs Code.:

Synonyms:Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

There total 9 articles about Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-hydroxy-6-(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: 76.0%

: 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

: 189144-53-4
Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With hydrazine dithiocarbonate; In 1,4-dioxane; at 23 ℃; for 1h;
DOI:10.1021/jo962300y

Reference yield:

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

: 189144-53-4
Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 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

7: 76 percent / hydrazine dithiocarbonate / dioxane / 1 h / 23 °C

With pyridine; 2,4,6-trimethyl-pyridine; tetrafluoroboric acid; hydrazine dithiocarbonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; In 1,4-dioxane; 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

: 189144-53-4
Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-hydroxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 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

8: 76 percent / hydrazine dithiocarbonate / dioxane / 1 h / 23 °C

With pyridine; 2,4,6-trimethyl-pyridine; tetrafluoroboric acid; zinc chloride diethyl ether; Dichloromethyl methyl ether; hydrazine dithiocarbonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo962300y