(1R,4S)-4-[(2R,4aS,6S,8aR)-6-((2R,5S)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-pentane-1,4-diol

Base Information

• Chemical Name: (1R,4S)-4-[(2R,4aS,6S,8aR)-6-((2R,5S)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-pentane-1,4-diol
• CAS No.: 93453-12-4
• Molecular Formula: C₃₀H₅₃BrO₇
• Molecular Weight: 605.651

Synonyms:

Chemical Property of (1R,4S)-4-[(2R,4aS,6S,8aR)-6-((2R,5S)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-pentane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S)-4-[(2R,4aS,6S,8aR)-6-((2R,5S)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-pentane-1,4-diol

There total 50 articles about (1R,4S)-4-[(2R,4aS,6S,8aR)-6-((2R,5S)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-pentane-1,4-diol 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: 42.0%

thyrsiferyl 18,23-diacetate (96304-94-8) → Thyrsiferyl-23-acetate (96304-95-9) + thyrsiferol (93453-12-4,105880-10-2,116502-09-1,66873-39-0)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 9h;

DOI:10.1021/ja000001r

Reference yield:

(2S,3S)-2,3-epoxygeraniol (82188-73-6) → thyrsiferol (93453-12-4,105880-10-2,116502-09-1,66873-39-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

1.2: 98 percent / Bu₄NI / tetrahydrofuran / 0 - 20 °C

2.1: 73 percent / aq. HClO₄ / tetrahydrofuran / 0 - 20 °C

3.1: 88 percent / pyridine / 18 h / 20 °C

4.1: 77 percent / Rhenium heptoxide; trifluoroacetic anhydride / CH₂Cl₂; acetonitrile

5.1: 70 percent / Sc(OTf)3 / acetonitrile / 0 - 20 °C

6.1: 98 percent / H₂ / Pd(OH)2/C / methanol; ethyl acetate / 2 h / 760.05 Torr

7.1: 88 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h / 20 °C

8.1: 88 percent / CrCl₂ / tetrahydrofuran / 16 h / 20 °C

9.1: 62 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 21 h / 20 °C

10.1: 88 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

11.1: 90 percent / H₂ / Pd/C / ethyl acetate / 5 h / 760.05 Torr

12.1: 87 percent / tetrahydrofuran; diethyl ether / 5 h / -78 °C

13.1: 42 percent / K₂CO₃ / methanol / 9 h / 20 °C

With pyridine; chromium dichloride; perchloric acid; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; rhenium(VII) oxide; trifluoroacetic anhydride; nickel dichloride; scandium tris(trifluoromethanesulfonate); palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1021/ja000001r

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → thyrsiferol (93453-12-4,105880-10-2,116502-09-1,66873-39-0)

Guidance literature:

Multi-step reaction with 21 steps

1.1: 74 percent / trifluoromethanesulfonic acid / CH₂Cl₂; pentane / 0.5 h / 0 °C

2.1: DIBAL / toluene / 1 h / -78 °C

3.1: 2.53 g / benzene / 2 h / Heating

4.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C

5.1: 72 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 86 percent / (-)-D-Diethyl tartrate; itanium isopropoxide; tert-butylhydroperoxide / 4 A molecular sieves / CH₂Cl₂; decane / 4 h / -20 °C

7.1: 95 percent / SO₃*Pyr; Et₃N / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

8.1: PPh₃ / CH₂Cl₂ / 0.33 h / 0 °C

8.2: 91 percent / NEt₃ / CH₂Cl₂ / 0.87 h / -78 °C

9.1: 88 percent / TBAF / tetrahydrofuran / 0 - 20 °C

10.1: 91 percent / borontrifluoride etherate / CH₂Cl₂ / -78 - -10 °C

11.1: 85 percent / imidazole / dimethylformamide / 0 - 20 °C

12.1: 75 percent / CrCl₂/NiCl₂ / dimethylformamide / 5 h / 20 °C

13.1: 89 percent / MnO₂ / hexane / 7 h / 20 °C

14.1: 98 percent / H₂ / Pd(OH)2/C / methanol / 2 h / 760.05 Torr

15.1: 76 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.5 h / -35 °C

16.1: 94 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

17.1: 62 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 21 h / 20 °C

18.1: 88 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

19.1: 90 percent / H₂ / Pd/C / ethyl acetate / 5 h / 760.05 Torr

20.1: 87 percent / tetrahydrofuran; diethyl ether / 5 h / -78 °C

21.1: 42 percent / K₂CO₃ / methanol / 9 h / 20 °C

With 1H-imidazole; chromium dichloride; titanium(IV) isopropylate; triethylsilane; tert.-butylhydroperoxide; manganese(IV) oxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; nickel dichloride; palladium dihydroxide; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; decane; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; pentane; benzene; 6.1: Sharpless asymmetric epoxidation;

DOI:10.1021/ja000001r

upstream raw materials:

thyrsifenyl 23-acetate

(2R,4aR,6R,8aS)-Octahydro-2-<(1S,4S)-1,4-dihydroxy-4-<(2R,5R)-tetrahydro-5-(1-hydroxy-1-methylethyl)-2-methylfuran-2-yl>-1-methylbutyl>-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

magireol-A

thyrsiferyl 18,23-diacetate

Downstream raw materials:

Acetic acid (1R,4S)-4-[(4aS,6S,8aR)-6-((2R,5S)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-hydroxy-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-pentyl ester

thyrsiferyl 18-acetate

thyrsiferol monoacetate

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