(1R,4S)-4-{(2R,4aR,6R,8aS)-6-[(2S,5R)-5-bromo-2,6,6-trimethyltetrahydro-2H-pyran-2-yl]-8a-methyloctahydropyrano[3,2-b]pyran-2-yl}-1-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]pentane-1,4-diol (non-preferred name)

Base Information

• Chemical Name: (1R,4S)-4-{(2R,4aR,6R,8aS)-6-[(2S,5R)-5-bromo-2,6,6-trimethyltetrahydro-2H-pyran-2-yl]-8a-methyloctahydropyrano[3,2-b]pyran-2-yl}-1-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]pentane-1,4-diol (non-preferred name)
• CAS No.: 105880-10-2
• Molecular Formula: C₃₀H₅₃BrO₇
• Molecular Weight: 605.651
• Mol file: 105880-10-2.mol

Synonyms:2,5-Furandimethanol,a2-[3-[6-(5-bromotetrahydro-2,6,6-trimethyl-2H-pyran-2-yl)octahydro-8a-methylpyrano[3,2-b]pyran-2-yl]-3-hydroxybutyl]tetrahydro-a5,a5,2-trimethyl-, [2R-[2a[S*[R*(2R*,5S*)]],4ab,6a(2S*,5R*),8aa]]-;Pyrano[3,2-b]pyran, 2,5-furandimethanol deriv.; (+)-Venustatriol; Venustatriol

Chemical Property of (1R,4S)-4-{(2R,4aR,6R,8aS)-6-[(2S,5R)-5-bromo-2,6,6-trimethyltetrahydro-2H-pyran-2-yl]-8a-methyloctahydropyrano[3,2-b]pyran-2-yl}-1-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]pentane-1,4-diol (non-preferred name)

Chemical Property:

• Vapor Pressure: 1.26E-19mmHg at 25°C
• Boiling Point: 649.7°Cat760mmHg
• Flash Point: 346.7°C
• Density: 1.223g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,4S)-4-{(2R,4aR,6R,8aS)-6-[(2S,5R)-5-bromo-2,6,6-trimethyltetrahydro-2H-pyran-2-yl]-8a-methyloctahydropyrano[3,2-b]pyran-2-yl}-1-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]pentane-1,4-diol (non-preferred name)

There total 78 articles about (1R,4S)-4-{(2R,4aR,6R,8aS)-6-[(2S,5R)-5-bromo-2,6,6-trimethyltetrahydro-2H-pyran-2-yl]-8a-methyloctahydropyrano[3,2-b]pyran-2-yl}-1-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]pentane-1,4-diol (non-preferred name) 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: 83.0%

(S)-2-[(2R,4aR,6R,8aS)-6-((2S,5R)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-((1S,2R,7R)-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]dec-2-yl)-butan-2-ol (121710-07-4) → venustatriol (105880-10-2)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 40 ℃; for 9h;

DOI:10.1016/0040-4039(88)85113-X

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

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

thyrsiferol monoacetate

thyrsiferyl 18-acetate

Refernces

• 1、 Suzuki, Teruaki,Takeda, Satoshi,Suzuki, Minoru,Kurosawa, Etsuro,Kato, Arata,Imanaka, Yoshihiko. "Cytotoxic Squalene-Derived Polyethers from the Marine Red Alga Laurentia obtusa (Hudson) Lamouroux". . p. 361 - 364. Retrieved 1987.
• 2、 Hashimoto, Masaru,Kan, Toshiyuki,Nozaki, Koji,Yanagiya, Mitsutoshi,Shirahama, Harushia,Matsumoto, Takeshi. "Total Syntheses of (+)-Thyrsiferol, (+)-Thyrsiferyl 23-Acetate, and (+)-Venustatriol". . p. 5088 - 5107. Retrieved 2007/10/02.
• 3、 Hashimoto,Kan,Nozaki,Yanagiya,Shirahama,Matsumoto. "Total synthesis of (+)-thyrsiferol and (+)-venustatriol". . p. 1143 - 1144. Retrieved 2007/10/02.