(5S,6S)-6-{(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-methyl-hept-1-en-4-one

Base Information

• Chemical Name: (5S,6S)-6-{(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-methyl-hept-1-en-4-one
• CAS No.: 201667-93-8
• Molecular Formula: C₃₄H₄₈O₇
• Molecular Weight: 568.751
• Mol file: 201667-93-8.mol

Synonyms:

Chemical Property of (5S,6S)-6-{(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-methyl-hept-1-en-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-6-{(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-methyl-hept-1-en-4-one

There total 34 articles about (5S,6S)-6-{(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-methyl-hept-1-en-4-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:

(2S,3S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol (201667-73-4) → (5S,6S)-6-{(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-methyl-hept-1-en-4-one (201667-93-8)

Guidance literature:

Multi-step reaction with 18 steps

1: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2) CH₂Cl₂, 0 deg C, 20 min

2: 88 percent / BuLi / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

3: 98 percent / H₂ / Lindlar catalyst / methanol / 48 h / 760 Torr / Ambient temperature

4: 100 percent / DMAP, NEt₃ / CH₂Cl₂ / 15 h / Ambient temperature

5: 63 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

6: 90 percent / pyridinium dichromate, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

7: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 0 °C

8: 34.0 mg / KOH / methanol; H₂O / 24 h / Ambient temperature

9: 1) 2,4,6-trichlorobenzoyl chloride, NEt₃, 2) DMAP / 1) toluene, room temperature, 18 h, 2) toluene, room temperature, 1 h

11: 92 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 - 20 °C

12: 95 percent / KH, TBAI / tetrahydrofuran / 2 h / Heating

13: 75 percent / 1 M aq. HCl / methanol / 3 h / Ambient temperature

14: 71 percent / NEt₃, DMAP / CH₂Cl₂ / 26 h / Ambient temperature

15: 100 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

16: 76 percent / dimethylsulfoxide / 4 h / Ambient temperature

17: 95 percent / H₂ / Lindlar catalyst / benzene / 0.5 h / 760 Torr / Ambient temperature

18: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) CH₂Cl₂, 0 deg C, 30 min

With hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(97)10253-8

Reference yield:

(2S,3S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyraldehyde (201667-71-2) → (5S,6S)-6-{(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-methyl-hept-1-en-4-one (201667-93-8)

Guidance literature:

Multi-step reaction with 17 steps

1: 88 percent / BuLi / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

2: 98 percent / H₂ / Lindlar catalyst / methanol / 48 h / 760 Torr / Ambient temperature

3: 100 percent / DMAP, NEt₃ / CH₂Cl₂ / 15 h / Ambient temperature

4: 63 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

5: 90 percent / pyridinium dichromate, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

6: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 0 °C

7: 34.0 mg / KOH / methanol; H₂O / 24 h / Ambient temperature

8: 1) 2,4,6-trichlorobenzoyl chloride, NEt₃, 2) DMAP / 1) toluene, room temperature, 18 h, 2) toluene, room temperature, 1 h

10: 92 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 - 20 °C

11: 95 percent / KH, TBAI / tetrahydrofuran / 2 h / Heating

12: 75 percent / 1 M aq. HCl / methanol / 3 h / Ambient temperature

13: 71 percent / NEt₃, DMAP / CH₂Cl₂ / 26 h / Ambient temperature

14: 100 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

15: 76 percent / dimethylsulfoxide / 4 h / Ambient temperature

16: 95 percent / H₂ / Lindlar catalyst / benzene / 0.5 h / 760 Torr / Ambient temperature

17: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) CH₂Cl₂, 0 deg C, 30 min

With hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(97)10253-8

Reference yield:

((2R,3R)-3-((R)-1-(Benzyloxy)propan-2-yl)oxiran-2-yl)methanol → (5S,6S)-6-{(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-methyl-hept-1-en-4-one (201667-93-8)

Guidance literature:

Multi-step reaction with 22 steps

1: CH₂Cl₂; hexane / 17 h / Ambient temperature

2: 1.18 g / NEt₃, DMAP / CH₂Cl₂ / 17 h / Ambient temperature

3: 93 percent / p-toluenesulfonic acid monohydrate / acetone / 36 h / Ambient temperature

4: 87 percent / H₂ / Pd-C / ethanol / 24 h / 760 Torr / Ambient temperature

5: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2) CH₂Cl₂, 0 deg C, 20 min

6: 88 percent / BuLi / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

7: 98 percent / H₂ / Lindlar catalyst / methanol / 48 h / 760 Torr / Ambient temperature

8: 100 percent / DMAP, NEt₃ / CH₂Cl₂ / 15 h / Ambient temperature

9: 63 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

10: 90 percent / pyridinium dichromate, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

11: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 0 °C

12: 34.0 mg / KOH / methanol; H₂O / 24 h / Ambient temperature

13: 1) 2,4,6-trichlorobenzoyl chloride, NEt₃, 2) DMAP / 1) toluene, room temperature, 18 h, 2) toluene, room temperature, 1 h

15: 92 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 - 20 °C

16: 95 percent / KH, TBAI / tetrahydrofuran / 2 h / Heating

17: 75 percent / 1 M aq. HCl / methanol / 3 h / Ambient temperature

18: 71 percent / NEt₃, DMAP / CH₂Cl₂ / 26 h / Ambient temperature

19: 100 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

20: 76 percent / dimethylsulfoxide / 4 h / Ambient temperature

21: 95 percent / H₂ / Lindlar catalyst / benzene / 0.5 h / 760 Torr / Ambient temperature

22: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 1 h, 2) CH₂Cl₂, 0 deg C, 30 min

With hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(97)10253-8

upstream raw materials:

(4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3''-hydroxy-5''-hexenyl)-1,3-dioxane

(2S,3S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol

(2S,3S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyraldehyde

(R)-1-methoxy-4-((3-methylpent-4-ynyloxy)methyl)benzene

Downstream raw materials:

(2R,3S,4S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-{(4R,5S,6S)-5-(4-methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-methyl-pentan-2-ol