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

Base Information

• Chemical Name: methyl (2E,4S,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-4,6-dimethyl-2-heptenoate
• CAS No.: 214060-11-4
• Molecular Formula: C₃₅H₄₆O₆Si
• Molecular Weight: 590.832

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about methyl (2E,4S,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-4,6-dimethyl-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:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → methyl (2E,4S,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-4,6-dimethyl-2-heptenoate (214060-11-4)

Guidance literature:

Multi-step reaction with 9 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: 1.) CuCN / 1.) THF, Et₂O, -30 deg C, 30 min, 2.) THF, Et₂O, a) from -35 deg C to RT, 2 h, b) RT, 12 h

3: 100 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 0.25 h / Ambient temperature

4: 98 percent / DIBAH / CH₂Cl₂; hexane / 24 h / -30 °C

5: Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / Ambient temperature

6: LiAlH₄ / tetrahydrofuran / Ambient temperature

7: 98 percent / OsO₄, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; acetone / 21 h / Ambient temperature

8: aq. NaIO₄ / methanol / 6 h / Ambient temperature

9: benzene / 12 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.47.308

Reference yield:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) → methyl (2E,4S,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-4,6-dimethyl-2-heptenoate (214060-11-4)

Guidance literature:

Multi-step reaction with 11 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: 1.) CuCN / 1.) THF, Et₂O, -30 deg C, 30 min, 2.) THF, Et₂O, a) from -35 deg C to RT, 2 h, b) RT, 12 h

5: 100 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 0.25 h / Ambient temperature

6: 98 percent / DIBAH / CH₂Cl₂; hexane / 24 h / -30 °C

7: Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / Ambient temperature

8: LiAlH₄ / tetrahydrofuran / Ambient temperature

9: 98 percent / OsO₄, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; acetone / 21 h / Ambient temperature

10: aq. NaIO₄ / methanol / 6 h / Ambient temperature

11: benzene / 12 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.47.308

Reference yield:

(R)-methyl 3-(tert-butyl(diphenyl)silyloxy)-2-methylpropanoate (95514-03-7) → methyl (2E,4S,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-4,6-dimethyl-2-heptenoate (214060-11-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 100 percent / LiBH₄ / diethyl ether / 70 h / Ambient temperature

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

3: 98 percent / benzene / 17 h / Ambient temperature

4: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 - -60 °C

5: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

6: 1.) CuCN / 1.) THF, Et₂O, -30 deg C, 30 min, 2.) THF, Et₂O, a) from -35 deg C to RT, 2 h, b) RT, 12 h

7: 100 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 0.25 h / Ambient temperature

8: 98 percent / DIBAH / CH₂Cl₂; hexane / 24 h / -30 °C

9: Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / Ambient temperature

10: LiAlH₄ / tetrahydrofuran / Ambient temperature

11: 98 percent / OsO₄, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; acetone / 21 h / Ambient temperature

12: aq. NaIO₄ / methanol / 6 h / Ambient temperature

13: benzene / 12 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium borohydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.47.308

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

(2R,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(3,4-dimethoxy-benzyloxy)-2,4-dimethyl-pentanal

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

Downstream raw materials:

methyl (2R,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate

methyl (2S,3R,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate

(E)-(4S,5R,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid methyl ester

methyl (2E,4S,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-methoxymethoxy-4,6-dimethyl-2-heptenoate

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