(3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione

Base Information

• Chemical Name: (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione
• CAS No.: 60325-08-8
• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.268
• Mol file: 60325-08-8.mol

Synonyms:(3aS,5S,11bS)-7-Hydroxy-5-methyl-3,3a,5,11b-tetrahydro-1,4-dioxa-cyclopenta[a]anthracene-2,6,11-trione;nanaomycin D;

Chemical Property of (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione

Chemical Property:

• PSA: 89.90000
• LogP: 1.17060

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione

There total 31 articles about (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione 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: 75.0%

epi-7-O-Methylkalafungin (226213-84-9) → Kalafungin (29394-61-4,60325-08-8,77448-27-2,11048-15-0)

Guidance literature:

With boron tribromide; In dichloromethane; at -50 - 20 ℃; for 2.41667h;

DOI:10.1055/s-2005-868505

Reference yield:

5-epi-kalafungin → Kalafungin (29394-61-4,60325-08-8,77448-27-2,11048-15-0)

Guidance literature:

With sulfuric acid; In benzene; for 0.5h;

DOI:10.1016/j.tetlet.2007.10.058

Reference yield:

1-(1,4,5-trimethoxy-naphthalen-2-yl)-prop-2-en-1-ol (859234-20-1) → Kalafungin (29394-61-4,60325-08-8,77448-27-2,11048-15-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 8 h / 20 °C

2.1: NaBr; Ph₃P; i-Pr₂NEt / Pd₂(dba)3 / 6 h / 50 °C

2.2: (DHQD)2-PHAL; K₃Fe(CN)6; aq. K₂CO₃ / MeSO₂NH₂; K₂Os₂(OH)4 / 2-methyl-propan-2-ol / 36 h / 0 - 20 °C

3.1: 92 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / 12 h / 20 °C

4.1: 87 percent / aq. (NH₄)2Ce(NO₃)6 / acetonitrile / 0.25 h / 20 °C

5.1: 75 percent / BBr₃ / CH₂Cl₂ / 2.42 h / -50 - 20 °C

With dmap; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; boron tribromide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bromide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 2.2: Sharpless' asymmetric dihydroxylation / 3.1: oxa-Pictet-Spengler cyclization;

DOI:10.1055/s-2005-868505

upstream raw materials:

9-O-Methylnanaomycin

(3aS,5R,11bS)-7-Methoxy-5-methyl-3,3a,5,11b-tetrahydro-1,4-dioxa-cyclopenta[a]anthracene-2,6,11-trione

1-(1,4,5-trimethoxy-naphthalen-2-yl)-prop-2-en-1-ol

acetic acid 1-(1,4,5-trimethoxy-naphthalen-2-yl)-allyl ester

Downstream raw materials:

4-deoxykalafunginic acid

Refernces

• 1、 Fernandes, Rodney A.,Chavan, Vijay P.,Mulay, Sandip V.,Manchoju, Amarender. "A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin". . p. 10455 - 10460. Retrieved 2013/01/15.
• 2、 Donner, Christopher D.. "Total synthesis of (+)-kalafungin using a tandem Michael-Dieckmann approach". . p. 8888 - 8890. Retrieved 2008/03/30.