Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester

Base Information

Chemical Name:Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester
CAS No.:218965-72-1
Molecular Formula:C₃₀H₄₁NO₁₀
Molecular Weight:575.656
Hs Code.:

Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester

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Chemical Property of Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester

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Technology Process of Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester

There total 22 articles about Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl 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:

: C₃₆H₄₇NO₁₁Se

: 218965-72-1
Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester

Guidance literature:: With triethylamine; In toluene; for 0.0416667h; Yield given; Heating;
DOI:10.1055/s-1998-1970

Reference yield:

: 207276-55-9
(+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

: 218965-72-1
Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: PDC / dimethylformamide / 23 h / 20 °C

2: 171 mg / (PhO)2PON₃; DIPEA; 4 Angstroem molecular sieves / toluene / 1 h / 65 °C

3: 66 percent / DMAP / CH₂Cl₂ / 91 h / 20 °C

4: 83 percent / TBAF*3H₂O / tetrahydrofuran / 0.03 h / 0 °C

5: 80 mg

6: LiBH(s-Bu)3 / tetrahydrofuran / 0.25 h / -95 °C

7: CSA / CH₂Cl₂ / 0.67 h / 20 °C

8: DMAP; DIPEA; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

9: hydroquinine 9-phenanthryl ether; potassium osmate dihydrate; aq. K₃Fe(CN)6 / 2-methyl-propan-2-ol / 8 h / 20 °C

10: aq. NaIO₄ / methanol / 1 h / 20 °C

11: 27 mg / Et₃N / toluene / 0.03 h / Heating

With dmap; potassium osmate(VI); sodium periodate; dipyridinium dichromate; 4 A molecular sieve; diphenyl phosphoryl azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; L-Selectride; dihydroquinine 9-O-(9'-phenanthryl) ether; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: Oxidation / 2: Rearrangement / 3: Acylation / 4: Hydrolysis / 6: Reduction / 7: Addition / 8: Acylation / 9: Oxidation / 10: Oxidation / 11: Elimination;
DOI:10.1039/a909898d

Reference yield:

: 210691-88-6
(1R,5R,6R,8R,10S)-5-(tert-Butylcarbonyloxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

: 218965-72-1
Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 98 percent / Red-Al / tetrahydrofuran; toluene / 0.5 h / -78 - 0 °C

2: PDC / dimethylformamide / 23 h / 20 °C

3: 171 mg / (PhO)2PON₃; DIPEA; 4 Angstroem molecular sieves / toluene / 1 h / 65 °C

4: 66 percent / DMAP / CH₂Cl₂ / 91 h / 20 °C

5: 83 percent / TBAF*3H₂O / tetrahydrofuran / 0.03 h / 0 °C

6: 80 mg

7: LiBH(s-Bu)3 / tetrahydrofuran / 0.25 h / -95 °C

8: CSA / CH₂Cl₂ / 0.67 h / 20 °C

9: DMAP; DIPEA; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

10: hydroquinine 9-phenanthryl ether; potassium osmate dihydrate; aq. K₃Fe(CN)6 / 2-methyl-propan-2-ol / 8 h / 20 °C

11: aq. NaIO₄ / methanol / 1 h / 20 °C

12: 27 mg / Et₃N / toluene / 0.03 h / Heating

With dmap; potassium osmate(VI); sodium periodate; dipyridinium dichromate; 4 A molecular sieve; diphenyl phosphoryl azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; L-Selectride; dihydroquinine 9-O-(9'-phenanthryl) ether; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: Substitution / 2: Oxidation / 3: Rearrangement / 4: Acylation / 5: Hydrolysis / 7: Reduction / 8: Addition / 9: Acylation / 10: Oxidation / 11: Oxidation / 12: Elimination;
DOI:10.1039/a909898d