xylomollin

Base Information

• Chemical Name: xylomollin
• CAS No.: 61229-34-3
• Molecular Formula: C₁₂H₁₈O₇
• Molecular Weight: 274.271
• Mol file: 61229-34-3.mol

Synonyms:1H,3H-Pyrano[3,4-c]pyran-4-carboxylicacid, hexahydro-1-hydroxy-3-methoxy-8-methyl-6-oxo-, methyl ester, [1R-(1a,3b,4a,4aa,8b,8ab)]-; NSC 280415; Xylomollin

Chemical Property of xylomollin

Chemical Property:

• Vapor Pressure: 2.55E-09mmHg at 25°C
• Boiling Point: 433.1°C at 760 mmHg
• Flash Point: 164.1°C
• PSA: 91.29000
• Density: 1.3g/cm³
• LogP: -0.33550

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of xylomollin

There total 15 articles about xylomollin 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:

cis-Bicyclo<3.3.0>octa-2,6-diene (17618-97-2,41527-66-6,104393-61-5,110269-92-6) → (-)-xylomollin (61229-34-3,74868-10-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.25 eq. SnCl₄ / 3.5 h / -78 °C

2: 83 percent / LiAlH₄ / tetrahydrofuran

3: 0.04 eq. DMAP, 1.1 eq. Et₃N / CH₂Cl₂ / 8 h / 0 - 5 °C

4: pyridine / 8 h / 0 - 5 °C

5: n-Bu₄NF / tetrahydrofuran / 8 h / 25 °C

6: 3 eq. LiBHEt₃ / tetrahydrofuran / 2 h / 0 °C

7: 95 percent / 0.01 eq. osmium tetraoxide, 1 eq. N-methylmorpholine N-oxide / acetone; H₂O / 8 h / 25 °C

With pyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tin(IV) chloride; lithium triethylborohydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1021/ja00281a057

Reference yield:

(R)-(1R,3aR,6aR)-2-(1,3a,6,6a-Tetrahydro-pentalen-1-yl)-oxirane (104393-71-7) → (-)-xylomollin (61229-34-3,74868-10-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 3 eq. LiBHEt₃ / tetrahydrofuran / 2 h / 0 °C

2: 95 percent / 0.01 eq. osmium tetraoxide, 1 eq. N-methylmorpholine N-oxide / acetone; H₂O / 8 h / 25 °C

With osmium(VIII) oxide; lithium triethylborohydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone;

DOI:10.1021/ja00281a057

Reference yield:

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(1R,3aR,6aR)-1,3a,6,6a-tetrahydro-pentalen-1-yl-ethanol (104393-64-8) → (-)-xylomollin (61229-34-3,74868-10-3)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 8 h / 0 - 5 °C

2: n-Bu₄NF / tetrahydrofuran / 8 h / 25 °C

3: 3 eq. LiBHEt₃ / tetrahydrofuran / 2 h / 0 °C

4: 95 percent / 0.01 eq. osmium tetraoxide, 1 eq. N-methylmorpholine N-oxide / acetone; H₂O / 8 h / 25 °C

With pyridine; osmium(VIII) oxide; tetrabutyl ammonium fluoride; lithium triethylborohydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone;

DOI:10.1021/ja00281a057

upstream raw materials:

methanol

(1R,4aS,8S,8aS)-1-Hydroxy-8-methyl-6-oxo-5,6,8,8a-tetrahydro-1H,4aH-pyrano[3,4-c]pyran-4-carboxylic acid methyl ester

cis-Bicyclo<3.3.0>octa-2,6-diene

(R)-(1R,3aR,6aR)-2-(1,3a,6,6a-Tetrahydro-pentalen-1-yl)-oxirane

Refernces

• 1、 Hassam, Saifunnissa B.,Hutchinson, C. Richard. "BIOMIMETIC CHEMISTRY OF XYLOMOLLIN". . p. 1209 - 1212. Retrieved 2007/10/02.