(2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran
• CAS No.: 198057-17-9
• Molecular Formula: C₃₂H₅₆O₆Si₂
• Molecular Weight: 592.964

Synonyms:

Chemical Property of (2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran

There total 36 articles about (2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran 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:

(Z)-(4S,5S)-5,6-Dihydroxy-4-(4-methoxy-benzyloxy)-hex-2-enoic acid methyl ester (198057-22-6) → (2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran (198057-17-9)

Guidance literature:

Multi-step reaction with 32 steps

1: 96 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

2: 95 percent / TsOH*H₂O / benzene / 17 h / Ambient temperature

3: 1.) DIBAH, 2.) dl-CSA / 1.) n-hexane, toluene, -78 deg C, 1 h, 2.) RT, 30 min

4: 97 percent / DDQ, phosphate buffer / methanol / 1 h / Ambient temperature

5: 74 percent / MCPBA, 4,4'-thiobis(6-tert-butyl-m-cresol) / CH₂Cl₂ / 40 h / Heating

6: 1.) Et₂O, THF, 0 deg C, 1 h, 2.) Et₂O, THF, RT, 3 d

7: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

8: 100 percent / TBAF, AcOH / tetrahydrofuran / 5 h / Ambient temperature

9: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / Ambient temperature

10: 97 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

11: 93 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / Ambient temperature

12: 87 percent / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 7 h / 760 Torr / Ambient temperature

13: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -40 deg C, 40 min

14: 1.) t-BuOK / 1.) THF, -20 deg C, 30 min, 2.) THF, RT, 40 min

15: 1.) disiamylborane, 2.) 15percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 7 h, 2.) THF, RT, 10 h

16: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) -40 deg C, 30 min

17: 1.) t-BuOK / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 20 min

18: 97 percent / DIBAH / tetrahydrofuran; CH₂Cl₂ / 4.5 h / -78 °C

19: 91 percent / D-(-)-diethyl tartrate, (i-PrO)4Ti, t-butylhydroperoxide, MS 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / 24 h

20: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

21: 97 percent / NaI, NaHCO₃ / butan-2-one / 12 h / 60 °C

22: 94 percent / t-BuLi / toluene; diethyl ether / 1 h / -78 °C

23: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

24: OsO₄, N-methylmorpholine N-oxide hydrate, H₂O / 2-methyl-propan-2-ol; acetone / 4 h / Ambient temperature

25: aq. NaIO₄ / tetrahydrofuran / 12 h / Ambient temperature

26: NaBH₄ / tetrahydrofuran / 1 h / Ambient temperature

27: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

28: 85 percent / BF₃*Et₂O, allyltriemthylsilane / acetonitrile / 0.25 h / Ambient temperature

29: 80 percent / BF₃*Et₂O, TMSOTf / acetonitrile / 3 h / 0 °C

30: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

31: K₂CO₃ / methanol / 0.5 h / Ambient temperature

32: CSA / benzene / 2 h / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; Santonox R; 2,6-di-tert-butyl-pyridine; phosphate buffer; oxalyl dichloride; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; DL-10-camphorsulfonic acid; MS 4 Angstroem; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; allyl-trimethyl-silane; palladium dihydroxide; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; butanone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.45.1558

Reference yield:

(3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene (198057-20-4) → (2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran (198057-17-9)

Guidance literature:

Multi-step reaction with 35 steps

1: 1.) N-BuLi / 1.) n-hexane, THF, -78 deg C, 1 h, 2.) n-hexane, THF, from -78 deg C, 30 min to RT, 1 h

2: 90 percent / H₂, quinoline / 5percent Pd/BaSO₄ / ethyl acetate / 0.25 h

3: 98 percent / 1N aq. HCl / methanol / 2 h / Ambient temperature

4: 96 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

5: 95 percent / TsOH*H₂O / benzene / 17 h / Ambient temperature

6: 1.) DIBAH, 2.) dl-CSA / 1.) n-hexane, toluene, -78 deg C, 1 h, 2.) RT, 30 min

7: 97 percent / DDQ, phosphate buffer / methanol / 1 h / Ambient temperature

8: 74 percent / MCPBA, 4,4'-thiobis(6-tert-butyl-m-cresol) / CH₂Cl₂ / 40 h / Heating

9: 1.) Et₂O, THF, 0 deg C, 1 h, 2.) Et₂O, THF, RT, 3 d

10: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

11: 100 percent / TBAF, AcOH / tetrahydrofuran / 5 h / Ambient temperature

12: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / Ambient temperature

13: 97 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

14: 93 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / Ambient temperature

15: 87 percent / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 7 h / 760 Torr / Ambient temperature

16: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -40 deg C, 40 min

17: 1.) t-BuOK / 1.) THF, -20 deg C, 30 min, 2.) THF, RT, 40 min

18: 1.) disiamylborane, 2.) 15percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 7 h, 2.) THF, RT, 10 h

19: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) -40 deg C, 30 min

20: 1.) t-BuOK / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 20 min

21: 97 percent / DIBAH / tetrahydrofuran; CH₂Cl₂ / 4.5 h / -78 °C

22: 91 percent / D-(-)-diethyl tartrate, (i-PrO)4Ti, t-butylhydroperoxide, MS 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / 24 h

23: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

24: 97 percent / NaI, NaHCO₃ / butan-2-one / 12 h / 60 °C

25: 94 percent / t-BuLi / toluene; diethyl ether / 1 h / -78 °C

26: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

27: OsO₄, N-methylmorpholine N-oxide hydrate, H₂O / 2-methyl-propan-2-ol; acetone / 4 h / Ambient temperature

28: aq. NaIO₄ / tetrahydrofuran / 12 h / Ambient temperature

29: NaBH₄ / tetrahydrofuran / 1 h / Ambient temperature

30: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

31: 85 percent / BF₃*Et₂O, allyltriemthylsilane / acetonitrile / 0.25 h / Ambient temperature

32: 80 percent / BF₃*Et₂O, TMSOTf / acetonitrile / 3 h / 0 °C

33: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

34: K₂CO₃ / methanol / 0.5 h / Ambient temperature

35: CSA / benzene / 2 h / Ambient temperature

With 1H-imidazole; quinoline; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; Santonox R; n-butyllithium; 2,6-di-tert-butyl-pyridine; phosphate buffer; oxalyl dichloride; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; DL-10-camphorsulfonic acid; MS 4 Angstroem; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; allyl-trimethyl-silane; palladium dihydroxide; Pd-BaSO₄; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; butanone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.45.1558

Reference yield:

(Z)-(S)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-but-2-enoic acid methyl ester (174968-18-4) → (2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran (198057-17-9)

Guidance literature:

Multi-step reaction with 33 steps

1: 98 percent / 1N aq. HCl / methanol / 2 h / Ambient temperature

2: 96 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

3: 95 percent / TsOH*H₂O / benzene / 17 h / Ambient temperature

4: 1.) DIBAH, 2.) dl-CSA / 1.) n-hexane, toluene, -78 deg C, 1 h, 2.) RT, 30 min

5: 97 percent / DDQ, phosphate buffer / methanol / 1 h / Ambient temperature

6: 74 percent / MCPBA, 4,4'-thiobis(6-tert-butyl-m-cresol) / CH₂Cl₂ / 40 h / Heating

7: 1.) Et₂O, THF, 0 deg C, 1 h, 2.) Et₂O, THF, RT, 3 d

8: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

9: 100 percent / TBAF, AcOH / tetrahydrofuran / 5 h / Ambient temperature

10: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / Ambient temperature

11: 97 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

12: 93 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / Ambient temperature

13: 87 percent / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 7 h / 760 Torr / Ambient temperature

14: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -40 deg C, 40 min

15: 1.) t-BuOK / 1.) THF, -20 deg C, 30 min, 2.) THF, RT, 40 min

16: 1.) disiamylborane, 2.) 15percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 7 h, 2.) THF, RT, 10 h

17: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) -40 deg C, 30 min

18: 1.) t-BuOK / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 20 min

19: 97 percent / DIBAH / tetrahydrofuran; CH₂Cl₂ / 4.5 h / -78 °C

20: 91 percent / D-(-)-diethyl tartrate, (i-PrO)4Ti, t-butylhydroperoxide, MS 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / 24 h

21: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

22: 97 percent / NaI, NaHCO₃ / butan-2-one / 12 h / 60 °C

23: 94 percent / t-BuLi / toluene; diethyl ether / 1 h / -78 °C

24: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

25: OsO₄, N-methylmorpholine N-oxide hydrate, H₂O / 2-methyl-propan-2-ol; acetone / 4 h / Ambient temperature

26: aq. NaIO₄ / tetrahydrofuran / 12 h / Ambient temperature

27: NaBH₄ / tetrahydrofuran / 1 h / Ambient temperature

28: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

29: 85 percent / BF₃*Et₂O, allyltriemthylsilane / acetonitrile / 0.25 h / Ambient temperature

30: 80 percent / BF₃*Et₂O, TMSOTf / acetonitrile / 3 h / 0 °C

31: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

32: K₂CO₃ / methanol / 0.5 h / Ambient temperature

33: CSA / benzene / 2 h / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; Santonox R; 2,6-di-tert-butyl-pyridine; phosphate buffer; oxalyl dichloride; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; DL-10-camphorsulfonic acid; MS 4 Angstroem; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; allyl-trimethyl-silane; palladium dihydroxide; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; butanone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.45.1558

upstream raw materials:

p-Anisaldehyde dimethyl acetal

(R)-3-[(2S,3S,4R,5R,6S)-6-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-tetrahydro-pyran-2-yl]-propane-1,2-diol

t-butyldimethylsiyl triflate

(2R,3R,4S,5S,6S)-6-benzyloxymethyloxymethyl-3,5-dihydroxy-2-methoxy-4-methyl-3,4,5,6-tetrahydro-2H-pyran

Downstream raw materials:

(R)-3-[(2S,3S,4R,5R,6S)-6-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-tetrahydro-pyran-2-yl]-2-(4-methoxy-benzyloxy)-propan-1-ol

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 198057-17-9 (2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran

Send

Send

Metric Ton KG G Pound L ML

Send

Send