11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol

Base Information

• Chemical Name: 11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol
• CAS No.: 676474-17-2
• Molecular Formula: C₄₃H₆₄O₆Si
• Molecular Weight: 705.063
• Mol file: 676474-17-2.mol

Synonyms:11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol

Chemical Property of 11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol

There total 24 articles about 11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol 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: 90.0%

(2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal (478490-93-6) + 2-(4-bromomethyl-2-methyl-pent-4-enyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran (676473-57-7) → 11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol (676474-17-2)

Guidance literature:

With hydrogenchloride; indium; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2003.12.001

Reference yield:

2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose (152453-72-0) → 11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol (676474-17-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: NaH / tetrahydrofuran / 0 °C

1.2: 85 percent / Bu₃P / acetonitrile / 60 °C

2.1: DIBAL / CH₂Cl₂ / -78 °C

3.1: 85 percent / pyridine / CH₂Cl₂

4.1: aq. HCl / tetrahydrofuran

5.1: NaIO₄ / tetrahydrofuran; H₂O / 0 °C

6.1: NaClO₂; H₂NSO₃H / 2-methyl-propan-2-ol; H₂O / 0 °C

7.1: 50 percent / methanol; toluene

8.1: tetrahydrofuran / -78 °C

9.1: pyridine / CH₂Cl₂

10.1: 70 percent / Et₃N; LiCl / tetrahydrofuran / 0 - 20 °C

11.1: 70 percent / L-selectride / tetrahydrofuran / -78 °C

12.1: 90 percent / imidazole / dimethylformamide / 0 °C

13.1: 80 percent / NaOMe / methanol / 0 °C

14.1: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

15.1: 90 percent / In; aq. HCl / tetrahydrofuran

With pyridine; 1H-imidazole; hydrogenchloride; indium; sodium chlorite; sodium periodate; oxalyl dichloride; aminosulfonic acid; sodium methylate; L-Selectride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.bmcl.2003.12.001

Reference yield:

acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester (362471-95-2) → 11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol (676474-17-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2: 70 percent / Ph₃P / CH₂Cl₂ / -78 °C

3: 80 percent / n-BuLi / tetrahydrofuran / -78 °C

4: 80 percent / Ph₃P; NBS / CH₂Cl₂ / 0 °C

5: 90 percent / In; aq. HCl / tetrahydrofuran

With hydrogenchloride; indium; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2003.12.001

upstream raw materials:

(2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal

2-(4-bromomethyl-2-methyl-pent-4-enyl)-6-prop-2-ynyl-3,6-dihydro-2H-pyran

2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose

acetic acid 4-methyl-2-methylene-5-[6-(2-oxo-ethyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester

Downstream raw materials:

6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-diene

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