16,18,20,22,24,26,28,30,32-Nonahydroxy-17,35-dimethyl-36-propan-2-yl-1-oxacyclohexatriaconta-3,5,7,9,11,13,33-heptaen-2-one

Base Information

• Chemical Name: 16,18,20,22,24,26,28,30,32-Nonahydroxy-17,35-dimethyl-36-propan-2-yl-1-oxacyclohexatriaconta-3,5,7,9,11,13,33-heptaen-2-one
• CAS No.: 51053-36-2
• Molecular Formula: C₄₀H₆₄O₁₁
• Molecular Weight: 720.942
• DSSTox Substance ID: DTXSID40965341
• Mol file: 51053-36-2.mol

Synonyms:BRN 1417386;C40H64O11;C40-H64-O11;DTXSID40965341;LS-59487;16,18,20,22,24,26,28,30,32-Nonahydroxy-17,35-dimethyl-36-(propan-2-yl)-1-oxacyclohexatriaconta-3,5,7,9,11,13,33-heptaen-2-one

Chemical Property of 16,18,20,22,24,26,28,30,32-Nonahydroxy-17,35-dimethyl-36-propan-2-yl-1-oxacyclohexatriaconta-3,5,7,9,11,13,33-heptaen-2-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 953°Cat760mmHg
• Flash Point: 282.9°C
• PSA: 208.37000
• Density: 1.119g/cm³
• LogP: 3.10230
• XLogP3: 5
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 1
• Exact Mass: 720.44486285
• Heavy Atom Count: 51
• Complexity: 1160

Purity/Quality:

98% ^*data from raw suppliers

DERMOSTATIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC(CC(CC(CC(CC(CC(CC(CC(C(C(CC=CC=CC=CC=CC=CC=CC(=O)OC1C(C)C)O)C)O)O)O)O)O)O)O)O

Technology Process of 16,18,20,22,24,26,28,30,32-Nonahydroxy-17,35-dimethyl-36-propan-2-yl-1-oxacyclohexatriaconta-3,5,7,9,11,13,33-heptaen-2-one

There total 21 articles about 16,18,20,22,24,26,28,30,32-Nonahydroxy-17,35-dimethyl-36-propan-2-yl-1-oxacyclohexatriaconta-3,5,7,9,11,13,33-heptaen-2-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: 77.0%

C58H94O11Si (375827-15-9) → dermostatin A (51053-36-2)

Guidance literature:

With Dowex-H⁺; In methanol; at 25 - 50 ℃;

DOI:10.1002/1521-3773(20010903)40:17<3224::AID-ANIE3224>3.0.CO;2-D

Reference yield: 76.0%

C67H94O13 → dermostatin A (51053-36-2)

Guidance literature:

With hydrogenchloride; In methanol; water; for 12h;

DOI:10.1021/jo2012658

Reference yield:

(4R)-5-bromo-4-(tert-butyldimethylsilanyloxy)-2-(trimethylsilanyloxy)pent-1-ene (375826-99-6) → dermostatin A (51053-36-2)

Guidance literature:

Multi-step reaction with 15 steps

1: BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -78 °C

2: SmI₂ / tetrahydrofuran / 0.33 h / -25 °C

3: 0.933 g / DIBAL-H / CH₂Cl₂; toluene / -78 - 0 °C

4: Dowex-50WX₈-100 acidic resin / methanol / 2 h / Heating

5: 0.182 g / dl-camphorsulfonic acid / acetone / 120 h / 20 °C

6: 65 percent / DMPU; LDA / tetrahydrofuran / 1.42 h / -78 - -50 °C

7: 70 percent / DMPU; LDA / tetrahydrofuran / 3 h / -78 - -50 °C

8: 75 percent / di-tert-butylbiphenyl; 2,2'-bipyridine; n-BuLi / lithium / tetrahydrofuran / 0.33 h / -78 °C

9: 88 percent / N-chlorosuccinimide; TEMPO; Bu₄NCl / NaHCO₃; Na₂CO₃ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 8.6

10: 88 percent / chromous chloride / dioxane; tetrahydrofuran / 3.5 h / 20 °C

11: 100 percent / 4-dimethylaminopyridine; BOP / CH₂Cl₂ / 48 h / 20 °C

12: 77 percent / diisopropylethylamine; triphenylarsine / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 3 h / 20 °C

13: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 20 °C

14: 2.0 mg / LiCl; DBU / acetonitrile / 36 h / 20 °C

15: 77 percent / Dowex 50WX₈-100 acidic resin / methanol / 26 h / 20 - 50 °C

With chromium dichloride; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; [2,2]bipyridinyl; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; n-butyllithium; samarium diiodide; triphenyl-arsane; di(tert-butyl)-biphenyl; Dowex 50WX₈-100 acidic resin; Dowex-50WX₈-100 acidic resin; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl-ammonium chloride; diisobutylaluminium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetone; toluene; acetonitrile; 1: Mukaiyama aldol addition / 9: Einhorn's modified TEMPO oxidation / 12: Stille coupling / 13: Dess-Martin oxidation / 14: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/S0040-4020(02)00666-X

upstream raw materials:

C₅₈H₉₄O₁₁Si

(4R)-5-bromo-4-(tert-butyldimethylsilanyloxy)-2-(trimethylsilanyloxy)pent-1-ene

C₁₅H₂₆Br₂O₄

(6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile