Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester
CAS No.:172276-07-2
Molecular Formula:C₂₀H₃₀O₁₁
Molecular Weight:446.452
Hs Code.:

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-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: 72.0%

: 1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9
(1R,2R)-trans-1,2-cyclohexanediol

: 74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7
2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

: 172276-07-2
Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; for 1h;
DOI:10.1016/S0040-4020(96)01178-7

Reference yield: 95.0%

: 116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8
ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

: 172276-07-2
Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester

: 172147-74-9
Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yl ester

Guidance literature:: With 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; for 24h;
DOI:10.1016/S0040-4020(96)01178-7

Reference yield:

: 172276-07-2
Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-3-yl ester

: 2-(2-{(2R,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3-yloxy}-ethyl)-malonic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / tetrabutylammonium bromide, molecular sieves 4 Angstroem, copper(II) bromide / CH₂Cl₂; dimethylformamide / 24 h

2: 98 percent / NaOMe / methanol / 3 h

3: 1.) dibutyltin oxide, 2.) tetrabutylammonium iodide / 1) methanol, reflux, 18 h; 2) toluene, 45 deg C, 17 h

4: 89 percent / p-toluenesulfonic acid / acetonitrile / 1 h

5: 1.) NaH / 1) DMF, 1 h; 2) DMF, 18 h

6: 83 percent / Wilkinson catalyst / ethanol; H₂O / 3 h / Heating

7: 95 percent / Ph₃P, Et₃N, 1,2-dibromo-tetrachloroethane / CH₂Cl₂ / 2 h

8: 92 percent / potassium carbonate, dibenzo-18-crown-6 / 5 h / 95 °C

9: H₂ / palladium on carbon / methanol; dioxane; acetic acid / 24 h

10: 80 percent / aq. NaOH / 2 h

With sodium hydroxide; Wilkinson's catalyst; dibenzo-18-crown-6; 1,2-dibromo-1,1,2,2-tetrachloroethane; 4 A molecular sieve; tetrabutylammomium bromide; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; copper(ll) bromide; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(96)01178-7