13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal

Base Information

Chemical Name:13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal
CAS No.:110561-04-1
Molecular Formula:C₃₇H₆₀O₆S₂
Molecular Weight:665.012
Hs Code.:

13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal

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Chemical Property of 13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal

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Technology Process of 13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal

There total 22 articles about 13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal 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: 71.2%

: 98-88-4
benzoyl chloride

: 110561-06-3
(2R,3S,4R)-6-{2-[(R)-(R)-3-(1,5-Dioxa-spiro[5.5]undec-2-yl)-butyl]-[1,3]dithian-2-yl}-3-(1-ethoxy-ethoxy)-2,4-dimethyl-heptan-1-ol

: 110561-04-1
13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal

Guidance literature:: With pyridine; Ambient temperature;
DOI:10.1016/S0040-4020(01)88109-6

Reference yield:

: 51385-38-7
(2S,3R,6S)-6-(hydroxymethyl)-2-methoxy-3,6-dihydro-2H-pyran-3-ol

: 110561-04-1
13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal

Guidance literature:: Multi-step reaction with 17 steps

1: 1.) MnO₂; 2.) pyridinium p-toluenesulfonate / 1.) CH₂Cl₂; 2.) CH₂Cl₂, room temp., 4 h.

2: 87.6 percent / CuI / diethyl ether / 0.33 h

3: 80 percent / n-BuLi / tetrahydrofuran; hexane / Ambient temperature

4: 1.) H₂; 2.) p-toluenesulfonic acid / 2.) 10percent Pd-C / 1.) ethyl acetate, 3.8 at; 2.) methanol, 0 - -5 deg C, 1.5 h.

5: 98.4 percent / pyridine / Ambient temperature

6: n-Bu₄NBr / dimethylformamide / 7 h / 80 °C

7: 57.1 percent / 30percent H₂O₂, 1N Na₂CO₃ / acetone / 72 h / Ambient temperature

8: 81.3 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

9: 74.7 percent / CH₂Cl₂ / Ambient temperature

10: LDA / tetrahydrofuran / 2 h / -78 °C

11: 1.) H₂SO₄; 2.) LiAlH₄ / 1.) MeOH, H₂O, 60 deg C, 11 h.; 2.) ether, reflux, 3 h.

12: BF₃*etherate / CH₂Cl₂ / Ambient temperature

13: 95.8 percent / imidazole / dimethylformamide / 2 h

14: 95.5 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

15: 69.8 percent / t-BuLi, HMPA / hexane; pentane / 1 h / 20 °C

16: 75 percent / n-Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

17: 71.2 percent / pyridine / Ambient temperature

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; pentane;
DOI:10.1016/S0040-4020(01)88109-6

Reference yield:

: 80532-19-0
methyl 3,4-dideoxy-6-O-(1-ethoxyethyl)-α-D-glycero-hex-3-enopyranosid-2-ulose

: 110561-04-1
13-O-benzoyl-1,3-O-cyclohexylidene-2,4,5,6,8,9,10,12-octadeoxy-11-O-(1-ethoxyethyl)-4,8,10,12-C-tetramethyl-D-gluco(and D-manno)-D-threo-7-trideculose trimethylene dithioacetal

Guidance literature:: Multi-step reaction with 16 steps

1: 87.6 percent / CuI / diethyl ether / 0.33 h

2: 80 percent / n-BuLi / tetrahydrofuran; hexane / Ambient temperature

3: 1.) H₂; 2.) p-toluenesulfonic acid / 2.) 10percent Pd-C / 1.) ethyl acetate, 3.8 at; 2.) methanol, 0 - -5 deg C, 1.5 h.

4: 98.4 percent / pyridine / Ambient temperature

5: n-Bu₄NBr / dimethylformamide / 7 h / 80 °C

6: 57.1 percent / 30percent H₂O₂, 1N Na₂CO₃ / acetone / 72 h / Ambient temperature

7: 81.3 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

8: 74.7 percent / CH₂Cl₂ / Ambient temperature

9: LDA / tetrahydrofuran / 2 h / -78 °C

10: 1.) H₂SO₄; 2.) LiAlH₄ / 1.) MeOH, H₂O, 60 deg C, 11 h.; 2.) ether, reflux, 3 h.

11: BF₃*etherate / CH₂Cl₂ / Ambient temperature

12: 95.8 percent / imidazole / dimethylformamide / 2 h

13: 95.5 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

14: 69.8 percent / t-BuLi, HMPA / hexane; pentane / 1 h / 20 °C

15: 75 percent / n-Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

16: 71.2 percent / pyridine / Ambient temperature

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; pentane;
DOI:10.1016/S0040-4020(01)88109-6