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

Base Information

Chemical Name:methyl (2S,3R,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate
CAS No.:214060-21-6
Molecular Formula:C₃₅H₄₈O₈Si
Molecular Weight:624.847
Hs Code.:

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

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

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

There total 15 articles about methyl (2S,3R,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate 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: 59.0%

: 214060-11-4
methyl (2E,4S,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-4,6-dimethyl-2-heptenoate

: 214060-19-2
methyl (2R,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate

: 214060-21-6
methyl (2S,3R,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; for 22h; Ambient temperature;
DOI:10.1248/cpb.47.308

Reference yield:

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

: 214060-21-6
methyl (2S,3R,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate

Guidance literature:: Multi-step reaction with 10 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

10: 59 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 22 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; water; acetone; tert-butyl alcohol; 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

: 214060-21-6
methyl (2S,3R,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate

Guidance literature:: Multi-step reaction with 12 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

12: 59 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 22 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; water; acetone; tert-butyl alcohol; benzene;
DOI:10.1248/cpb.47.308