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

Base Information

• Chemical Name: 2-[6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran
• CAS No.: 847835-01-2
• Molecular Formula: C₄₉H₇₈O₇Si₂
• Molecular Weight: 835.325

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

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

Chemical Property:

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

There total 27 articles about 2-[6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran 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: 80.0%

t-butyldimethylsiyl triflate (69739-34-0) + 11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-1-(3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dien-6-ol (849361-73-5) → 2-[6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran (847835-01-2)

Guidance literature:

With dmap; In pyridine;

DOI:10.1016/j.tetlet.2004.12.056

Reference yield:

(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)acetaldehyde (136787-40-1) → 2-[6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran (847835-01-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: p-TsOH / benzene / Heating

2.1: K₂CO₃ / methanol

3.1: imidazole / dimethylformamide / 10 °C

4.1: NaH / dimethylformamide

5.1: 75 percent / TBAF / tetrahydrofuran

6.1: 2,6-di-t-butylpyridine / CH₂Cl₂ / -50 °C

7.1: 80 percent / HMPA / tetrahydrofuran / -78 °C

8.1: Cs₂CO₃ / methanol

9.1: 70 percent / AgNO₃; NIS / acetone

10.1: NiCl₂; CrCl₂ / tetrahydrofuran

11.1: 80 percent / TPAP; NMO / CH₂Cl₂

12.1: 65 percent / [(Ph₃P)CuH]6 / toluene; H₂O

13.1: 90 percent / n-BuLi / tetrahydrofuran / 0 °C

14.1: 50 percent / aq. HOAc / 60 °C

15.1: Ph₃P / CH₂Cl₂ / -78 °C

15.2: n-BuLi / tetrahydrofuran / -78 °C

16.1: TBAF / tetrahydrofuran

17.1: 70 percent / Ph₃P; NBS / CH₂Cl₂ / 0 °C

18.1: 65 percent / HCl / indium / tetrahydrofuran; H₂O

19.1: 80 percent / DMAP / pyridine

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; N-Bromosuccinimide; N-iodo-succinimide; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; (triphenylphosphine)copper(I) hydride hexamer; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; silver nitrate; acetic acid; triphenylphosphine; chromium dichloride; indium; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene; 12.1: double Stryker-type reduction / 15.1: Corey-Fuchs reaction;

DOI:10.1016/j.tetlet.2004.12.056

Reference yield:

2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose (152453-72-0) → 2-[6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran (847835-01-2)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH / tetrahydrofuran / 0 °C

2: Bu₃P / acetonitrile / 60 °C

3: aq. HCl / tetrahydrofuran

4: 70 percent / NaIO₄ / tetrahydrofuran; H₂O / 0 °C

5: 60 percent / NiCl₂; CrCl₂ / dimethylsulfoxide

6: Dess-Martin periodinane / CH₂Cl₂

7: 50 percent / L-Selectride(R) / tetrahydrofuran / -78 °C

8: 90 percent / imidazole / dimethylformamide

9: 80 percent / DIBAL-H / CH₂Cl₂ / -78 °C

10: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

11: 65 percent / HCl / indium / tetrahydrofuran; H₂O

12: 80 percent / DMAP / pyridine

With 1H-imidazole; hydrogenchloride; dmap; sodium periodate; oxalyl dichloride; tributylphosphine; L-Selectride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; chromium dichloride; indium; nickel dichloride; In tetrahydrofuran; pyridine; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 1: Horner-Wadsworth-Emmons reaction / 10: Swern oxidation;

DOI:10.1016/j.tetlet.2004.12.056

upstream raw materials:

t-butyldimethylsiyl triflate

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

(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)acetaldehyde

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

Downstream raw materials:

4-{6-[6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

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