6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

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Chemical Name:6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
CAS No.:143747-01-7
Molecular Formula:C₃₂H₄₄O₆
Molecular Weight:524.698
Hs Code.:

6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

Synonyms:6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

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Chemical Property of 6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

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Technology Process of 6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

There total 9 articles about 6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one 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: 61.0%

: 143747-00-6
6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-<(tert-butyldimethylsilyl)oxy>benzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one

: 143747-01-7
6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 23 ℃; for 1.5h;
DOI:10.1021/jm00099a009

Reference yield:

: 5856-77-9
2,2-dimethylbutanoyl chloride

: 143747-01-7
6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 4-(dimethylamino)pyridine (DMAP), LiBr, pyridine / 30 h / 90 °C

2: 61 percent / 49percent aq. HF / acetonitrile / 1.5 h / 23 °C

With pyridine; dmap; hydrogen fluoride; lithium bromide; In acetonitrile;
DOI:10.1021/jm00099a009

Reference yield:

: 79902-31-1
(4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one

: 143747-01-7
6(R)-<2-<8(R)-<(2,2-dimethylbutanoyl)oxy>-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxybenzyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, 20 min

2: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3: H₂O / CH₂Cl₂ / 0.08 h

4: 32 percent / TiCl₄ / CH₂Cl₂ / 2.75 h / -70 - -45 °C

5: 57 percent / NaBH₄, PdCl₂ / tetrahydrofuran; H₂O / -30 - -5 °C

6: 78 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 10 °C

7: 4-(dimethylamino)pyridine (DMAP), LiBr, pyridine / 30 h / 90 °C

8: 61 percent / 49percent aq. HF / acetonitrile / 1.5 h / 23 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; hydrogen fluoride; water; titanium tetrachloride; dimethyl sulfoxide; triethylamine; lithium bromide; palladium dichloride; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jm00099a009