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

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R,6R)-5-((2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-3-allyloxy-4-benzyloxy-tetrahydro-pyran-2-yloxy)-2-acetoxymethyl-4-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester
CAS No.:189144-61-4
Molecular Formula:C₄₂H₅₈O₁₅Si
Molecular Weight:830.999
Hs Code.:

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

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

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

There total 23 articles about Acetic acid (2R,3R,4S,5R,6R)-5-((2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-3-allyloxy-4-benzyloxy-tetrahydro-pyran-2-yloxy)-2-acetoxymethyl-4-benzyloxy-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:

: 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

: 189144-61-4
Acetic acid (2R,3R,4S,5R,6R)-5-((2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-3-allyloxy-4-benzyloxy-tetrahydro-pyran-2-yloxy)-2-acetoxymethyl-4-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

2: 95 percent / NaOMe / methanol / 24 h / 23 °C

3: 96 percent / camphorsulfonic acid / dimethylformamide / 2 h / 23 °C

4: 96 percent / NaH / dimethylformamide / 1 h / 23 °C

5: 78 percent / tetrafluoroboric acid / methanol; ethyl acetate; diethyl ether / 0.5 h / 23 °C

6: 96 percent / pyridine / 1 h / 23 °C

7: 94 percent / α,α-dichloromethyl methyl ether, ZnCl2*Et2O / CH2Cl2 / 2 h / 0 °C

8: 1.) Ag₂CO₃, 4 Angstroem molecular sieves, 2.) AgClO₄ / 1) CH₂Cl₂, 23 deg C, 1 h; 2) CH₂Cl₂, 0 deg C, 48 h

With pyridine; tetrafluoroboric acid; zinc chloride diethyl ether; Dichloromethyl methyl ether; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; silver perchlorate; sodium hydride; silver carbonate; In methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo962300y

Reference yield:

: 58341-62-1
methyl 2-O-allyl-3-O-benzyl-α-D-glucopyranoside

: 189144-61-4
Acetic acid (2R,3R,4S,5R,6R)-5-((2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-3-allyloxy-4-benzyloxy-tetrahydro-pyran-2-yloxy)-2-acetoxymethyl-4-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 2 h / 23 °C

2: conc. H₂SO₄ / 0.05 h / 0 °C

3: 91 percent / α,α-dichloromethyl methyl ether, ZnCl2*Et2O / CH2Cl2 / 0.5 h / 23 °C

4: 1.) Ag₂CO₃, 4 Angstroem molecular sieves, 2.) AgClO₄ / 1) CH₂Cl₂, 23 deg C, 1 h; 2) CH₂Cl₂, 0 deg C, 48 h

With pyridine; zinc chloride diethyl ether; Dichloromethyl methyl ether; 4 A molecular sieve; sulfuric acid; silver perchlorate; silver carbonate; In dichloromethane;
DOI:10.1021/jo962300y

Reference yield:

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

: 189144-61-4
Acetic acid (2R,3R,4S,5R,6R)-5-((2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-3-allyloxy-4-benzyloxy-tetrahydro-pyran-2-yloxy)-2-acetoxymethyl-4-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 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

8: 1.) Ag₂CO₃, 4 Angstroem molecular sieves, 2.) AgClO₄ / 1) CH₂Cl₂, 23 deg C, 1 h; 2) CH₂Cl₂, 0 deg C, 48 h

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