[(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane

Base Information

• Chemical Name: [(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane
• CAS No.: 441352-20-1
• Molecular Formula: C₃₆H₅₄O₈Si
• Molecular Weight: 642.905

Synonyms:[(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane

Chemical Property of [(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of [(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane

There total 28 articles about [(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane 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:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → [(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane (441352-20-1)

Guidance literature:

Multi-step reaction with 26 steps

1.1: tetrahydrofuran / 3 h / Heating

2.1: H₂ / 10 percent Pd/C / ethyl acetate; methanol / 20 °C

3.1: 16.33 g / camphorsulfonic acid / CH₂Cl₂ / 20 °C

4.1: i-Pr₂NEt; tetra-n-butylammonium iodide / CH₂Cl₂ / 72 h / 20 °C

5.1: LiAlH₄ / tetrahydrofuran / 0.75 h / 0 °C

6.1: 20.42 g / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 - 20 °C

7.1: H₂ / 20 percent Pd/C / ethyl acetate; methanol / 20 °C

8.1: NaH / dimethylformamide / 0.5 h / 20 °C

8.2: tetra-n-butylammonium iodide / dimethylformamide / 20 °C

9.1: 14.03 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

10.1: Et₃N; SO₃*pyridine complex / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

11.1: BF₃*OEt₂; Me₂S / CH₂Cl₂ / 0.5 h / 0 °C

12.1: 259.0 mg / NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

13.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

13.2: 64 percent / DMAP / benzene / 4 h / Heating

14.1: 75 percent / HMPA; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

15.1: aq. NaHCO₃ / tetrahydrofuran / 0.25 h / 20 °C

15.2: Pd(PPh₃)4 / tetrahydrofuran; dimethylformamide / 20 h / 50 °C

15.3: 97 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 20 °C

16.1: 2,3-dimethyl-2-butene; BH₃*THF / tetrahydrofuran / -10 - 0 °C

16.2: 83 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h / 20 °C

17.1: 99 percent / 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

18.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

18.2: Et₃N / tetrahydrofuran / 0.17 h / -78 °C

19.1: 632.5 mg / Pd(OAc)2 / acetonitrile / 0.5 h / 20 °C

20.1: aq. HF / acetonitrile / 20 °C

20.2: BF₃*OEt₂; Et₃SiH

21.1: Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

22.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

22.2: 94.9 mg / tetrahydrofuran; CH₂Cl₂ / 0.5 h / 0 °C

23.1: lithium di-tert-butylbiphenylide / tetrahydrofuran / 1 h / -78 °C

24.1: 48.2 mg / camphorsulfonic acid / CH₂Cl₂; dimethylformamide / 6 h / 20 °C

25.1: 2,6-lutidine / dimethylformamide; CH₂Cl₂ / 6 h / 0 °C

26.1: NaHMDS / dimethylformamide; tetrahydrofuran / 0.5 h / 0 °C

26.2: 302.7 mg / dimethylformamide; tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 2,3-Dimethyl-2-butene; borane-THF; 2-methyl-but-2-ene; pyridine-SO₃ complex; dimethylsulfide; 4 A molecular sieve; lithium di-tert-butylbiphenylide; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(02)00045-5

Reference yield:

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester (116237-17-3) → [(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane (441352-20-1)

Guidance literature:

Multi-step reaction with 23 steps

1.1: i-Pr₂NEt; tetra-n-butylammonium iodide / CH₂Cl₂ / 72 h / 20 °C

2.1: LiAlH₄ / tetrahydrofuran / 0.75 h / 0 °C

3.1: 20.42 g / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 - 20 °C

4.1: H₂ / 20 percent Pd/C / ethyl acetate; methanol / 20 °C

5.1: NaH / dimethylformamide / 0.5 h / 20 °C

5.2: tetra-n-butylammonium iodide / dimethylformamide / 20 °C

6.1: 14.03 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

7.1: Et₃N; SO₃*pyridine complex / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

8.1: BF₃*OEt₂; Me₂S / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 259.0 mg / NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

10.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

10.2: 64 percent / DMAP / benzene / 4 h / Heating

11.1: 75 percent / HMPA; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

12.1: aq. NaHCO₃ / tetrahydrofuran / 0.25 h / 20 °C

12.2: Pd(PPh₃)4 / tetrahydrofuran; dimethylformamide / 20 h / 50 °C

12.3: 97 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 20 °C

13.1: 2,3-dimethyl-2-butene; BH₃*THF / tetrahydrofuran / -10 - 0 °C

13.2: 83 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h / 20 °C

14.1: 99 percent / 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

15.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

15.2: Et₃N / tetrahydrofuran / 0.17 h / -78 °C

16.1: 632.5 mg / Pd(OAc)2 / acetonitrile / 0.5 h / 20 °C

17.1: aq. HF / acetonitrile / 20 °C

17.2: BF₃*OEt₂; Et₃SiH

18.1: Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

19.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

19.2: 94.9 mg / tetrahydrofuran; CH₂Cl₂ / 0.5 h / 0 °C

20.1: lithium di-tert-butylbiphenylide / tetrahydrofuran / 1 h / -78 °C

21.1: 48.2 mg / camphorsulfonic acid / CH₂Cl₂; dimethylformamide / 6 h / 20 °C

22.1: 2,6-lutidine / dimethylformamide; CH₂Cl₂ / 6 h / 0 °C

23.1: NaHMDS / dimethylformamide; tetrahydrofuran / 0.5 h / 0 °C

23.2: 302.7 mg / dimethylformamide; tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 2,3-Dimethyl-2-butene; borane-THF; 2-methyl-but-2-ene; pyridine-SO₃ complex; dimethylsulfide; 4 A molecular sieve; lithium di-tert-butylbiphenylide; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(02)00045-5

Reference yield:

5(S), 6(R), 7-trihydroxyheptanoic acid methyl ester (78606-80-1) → [(2R,4aR,5aS,6aR,8S,9S,10R,10aR,11aR,13aS)-8-Allyl-9-allyloxy-2-(4-methoxy-phenyl)-4a,5a,6,6a,8,9,10,10a,11a,13a-decahydro-4H-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-10-yloxy]-triisopropyl-silane (441352-20-1)

Guidance literature:

Multi-step reaction with 24 steps

1.1: 16.33 g / camphorsulfonic acid / CH₂Cl₂ / 20 °C

2.1: i-Pr₂NEt; tetra-n-butylammonium iodide / CH₂Cl₂ / 72 h / 20 °C

3.1: LiAlH₄ / tetrahydrofuran / 0.75 h / 0 °C

4.1: 20.42 g / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 - 20 °C

5.1: H₂ / 20 percent Pd/C / ethyl acetate; methanol / 20 °C

6.1: NaH / dimethylformamide / 0.5 h / 20 °C

6.2: tetra-n-butylammonium iodide / dimethylformamide / 20 °C

7.1: 14.03 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

8.1: Et₃N; SO₃*pyridine complex / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

9.1: BF₃*OEt₂; Me₂S / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 259.0 mg / NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

11.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 20 °C

11.2: 64 percent / DMAP / benzene / 4 h / Heating

12.1: 75 percent / HMPA; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

13.1: aq. NaHCO₃ / tetrahydrofuran / 0.25 h / 20 °C

13.2: Pd(PPh₃)4 / tetrahydrofuran; dimethylformamide / 20 h / 50 °C

13.3: 97 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 20 °C

14.1: 2,3-dimethyl-2-butene; BH₃*THF / tetrahydrofuran / -10 - 0 °C

14.2: 83 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h / 20 °C

15.1: 99 percent / 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

16.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

16.2: Et₃N / tetrahydrofuran / 0.17 h / -78 °C

17.1: 632.5 mg / Pd(OAc)2 / acetonitrile / 0.5 h / 20 °C

18.1: aq. HF / acetonitrile / 20 °C

18.2: BF₃*OEt₂; Et₃SiH

19.1: Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

20.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

20.2: 94.9 mg / tetrahydrofuran; CH₂Cl₂ / 0.5 h / 0 °C

21.1: lithium di-tert-butylbiphenylide / tetrahydrofuran / 1 h / -78 °C

22.1: 48.2 mg / camphorsulfonic acid / CH₂Cl₂; dimethylformamide / 6 h / 20 °C

23.1: 2,6-lutidine / dimethylformamide; CH₂Cl₂ / 6 h / 0 °C

24.1: NaHMDS / dimethylformamide; tetrahydrofuran / 0.5 h / 0 °C

24.2: 302.7 mg / dimethylformamide; tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 2,3-Dimethyl-2-butene; borane-THF; 2-methyl-but-2-ene; pyridine-SO₃ complex; dimethylsulfide; 4 A molecular sieve; lithium di-tert-butylbiphenylide; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(02)00045-5

upstream raw materials:

allyl bromide

2-deoxy-D-ribose

p-Anisaldehyde dimethyl acetal

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

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