(+) Olivin

Base Information

• Chemical Name: (+) Olivin
• CAS No.: 121423-38-9
• Molecular Formula: C₂₀H₂₂O₉
• Molecular Weight: 406.389
• Mol file: 121423-38-9.mol

Synonyms:

Chemical Property of (+) Olivin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+) Olivin

There total 28 articles about (+) Olivin 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: 95.0%

3-<1'-<<1'(S),2'(R),3'(S),4'(R)>-3',4'--1'-methoxy-2'-oxopentyl>>-6,8,9-tris<(benzyloxy)methoxy>-1,2,3,4-tetrahydro-2-<(tert-butyldimethylsilyl)oxy>-1(2H)-anthracenone (111436-99-8) → (+) Olivin (6680-06-4,121423-38-9)

Guidance literature:

With Dowex 50W-X₈ resin; In methanol; for 144h;

DOI:10.1021/ja00190a036

Reference yield: 90.0%

(2S,3S)-6,8,9-Tris-benzyloxymethoxy-2-(tert-butyl-dimethyl-silanyloxy)-3-[(S)-1-methoxy-2-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-2-oxo-ethyl]-3,4-dihydro-2H-anthracen-1-one (111436-99-8) → olivin (6680-06-4,121423-38-9)

Guidance literature:

With Dowex 50W-X₈ H⁽¹⁺⁾ resin; In methanol; at 23 ℃; for 144h;

DOI:10.1021/ja00258a077

Reference yield:

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → olivin (6680-06-4,121423-38-9)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH / dimethylformamide

2: LiAlH₄ / tetrahydrofuran

3: NBS / CHCl₃ / Heating

4: n-BuLi, sec-BuLi / tetrahydrofuran / -78 °C

5: 1.) LDA, 2.) CH₃SO₂Cl, Et₃N / 1.) THF, -78 degC

6: 1.) NaH, 2.) 9-BBN, 3.) H₂O₂, NaOH, 4.) (COCl)2 / 1.) DMF, 2.) THF, 4.) DMSO

7: 1.) KMnO₄, 5percent KH₂PO₄ / 1.) t-BuOH

8: 1.) KO-t-Bu, 2.) 0.4M NaOH / 1.) C₆H₆, 23 degC, 2.) aq. EtOH, reflux

9: 93 percent / Bu₄NF / tetrahydrofuran / 23 °C

10: 90 percent / (COCl)2, DMSO

11: 1.) Et₃N, 2.) mCPBA

12: 90 percent / Dowex 50W-X₈ H⁽¹⁺⁾ resin / methanol / 144 h / 23 °C

With sodium hydroxide; potassium permanganate; potassium dihydrogenphosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; Dowex 50W-X₈ H⁽¹⁺⁾ resin; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; sec.-butyllithium; sodium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ja00258a077

upstream raw materials:

(2S,3S)-6,8,9-Tris-benzyloxymethoxy-2-(tert-butyl-dimethyl-silanyloxy)-3-[(S)-1-methoxy-2-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-2-oxo-ethyl]-3,4-dihydro-2H-anthracen-1-one

1-carbomethoxy-3,5-dihydroxybenzene

3(R),4(S),5(R),6(S),7(R)-4-Methoxy-6,7-dihydroxy-5-<(tert-butyldimethylsilyl)oxy>-3-vinyloctanal 6.7-cyclohexyl ketal

Methyl 5(R),6(S),7(R),8(S),9(R)-6-methoxy-8,9-dihydroxy-7-<(tert-butyldimethylsilyl)oxy>-5-vinyldec-2(E)-enoate 8,9-cyclohexyl ketal