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-chloro-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-chloro-tetrahydro-pyran-3-yl ester
CAS No.:189144-29-4
Molecular Formula:C₃₇H₄₅ClO₁₄
Molecular Weight:749.209
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-chloro-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-chloro-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-chloro-tetrahydro-pyran-3-yl ester

There total 26 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-chloro-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:

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

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

: 189144-29-4
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-chloro-tetrahydro-pyran-3-yl ester

Guidance literature:: With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 23 ℃; for 5h; Title compound not separated from byproducts;
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

: 189144-29-4
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-chloro-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 10 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

9: 87 percent / CF₃CO₂H / CH₂Cl₂ / 12 h / 23 °C

10: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 5 h / 23 °C

With pyridine; tetrafluoroboric acid; oxalyl dichloride; 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; trifluoroacetic acid; 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

: 189144-29-4
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-chloro-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 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

5: 87 percent / CF₃CO₂H / CH₂Cl₂ / 12 h / 23 °C

6: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 5 h / 23 °C

With pyridine; oxalyl dichloride; zinc chloride diethyl ether; Dichloromethyl methyl ether; 4 A molecular sieve; sulfuric acid; silver perchlorate; silver carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo962300y