methyl (2E,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-6-methyl-2-heptenoate

Base Information

Chemical Name:methyl (2E,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-6-methyl-2-heptenoate
CAS No.:214060-23-8
Molecular Formula:C₃₄H₄₄O₆Si
Molecular Weight:576.805
Hs Code.:

Synonyms:methyl (2E,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-6-methyl-2-heptenoate

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Chemical Property of methyl (2E,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-6-methyl-2-heptenoate

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Technology Process of methyl (2E,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-6-methyl-2-heptenoate

There total 11 articles about methyl (2E,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-6-methyl-2-heptenoate 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:

: 127665-68-3
(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

: 214060-23-8
methyl (2E,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-6-methyl-2-heptenoate

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

2: 86 percent / diborane / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / Ambient temperature

3: 92 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

4: 88 percent / DIBAH / CH₂Cl₂; hexane / a) from -50 deg C to -20 deg C, 2 h, b) -20 deg C, 1 h

5: Dess-Martin reagent, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

6: benzene / 12 h / Ambient temperature

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; Dess-Martin periodane; diborane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,4-trimethylpentane; hexane; dichloromethane; benzene;
DOI:10.1248/cpb.47.308

Reference yield:

: 91751-24-5,92817-88-4,123284-89-9,112897-04-8
(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

: 214060-23-8
methyl (2E,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-6-methyl-2-heptenoate

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / benzene / 17 h / Ambient temperature

2: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 - -60 °C

3: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

4: 86 percent / diborane / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / Ambient temperature

5: 92 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

6: 88 percent / DIBAH / CH₂Cl₂; hexane / a) from -50 deg C to -20 deg C, 2 h, b) -20 deg C, 1 h

7: Dess-Martin reagent, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

8: benzene / 12 h / Ambient temperature

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; Dess-Martin periodane; diborane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,4-trimethylpentane; hexane; dichloromethane; benzene;
DOI:10.1248/cpb.47.308

Reference yield:

: 95514-04-8,129029-85-2,120346-83-0
(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

: 214060-23-8
methyl (2E,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-6-methyl-2-heptenoate

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂ / 2 h / -78 - -55 °C

2: 98 percent / benzene / 17 h / Ambient temperature

3: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 - -60 °C

4: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

5: 86 percent / diborane / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / Ambient temperature

6: 92 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

7: 88 percent / DIBAH / CH₂Cl₂; hexane / a) from -50 deg C to -20 deg C, 2 h, b) -20 deg C, 1 h

8: Dess-Martin reagent, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

9: benzene / 12 h / Ambient temperature

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; diborane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,4-trimethylpentane; hexane; dichloromethane; benzene;
DOI:10.1248/cpb.47.308