Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester

Base Information

Chemical Name:Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester
CAS No.:497056-64-1
Molecular Formula:C₃₁H₅₂O₆Si
Molecular Weight:548.836
Hs Code.:

Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester

Synonyms:Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester

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Chemical Property of Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester

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Technology Process of Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester

There total 9 articles about Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester 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: 97.0%

: 99745-86-5,106357-20-4,106357-33-9,99687-40-8
(S,S)-diisopropyl tartrate (E)-crotylboronate

: 777096-25-0
Acetic acid (E)-(2R,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-formyl-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester

: 497056-64-1
Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester

Guidance literature:: In toluene; at -78 ℃; for 17h;
DOI:10.1021/ja0289649

Reference yield:

: 126889-55-2
diethyl(isopropyl)silyl trifluoromethanesulfonate

: 497056-64-1
Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-lutidine

2: LiBH₄ / methanol; diethyl ether

3: DMAP; Et₃N

4: OsO₄; NMO

5: aq. NaIO₄

6: 97 percent / toluene / 17 h / -78 °C

With 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; triethylamine; In methanol; diethyl ether; toluene; 6: Roush crotylation;
DOI:10.1021/ja0289649

Reference yield:

: 220213-54-7
(E)-(R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-pent-2-en-1-ol

: 497056-64-1
Acetic acid (E)-(2S,3S,6R)-3-(diethyl-isopropyl-silanyloxy)-2-((1R,2R)-1-hydroxy-2-methyl-but-3-enyl)-7-(4-methoxy-benzyloxy)-4,6-dimethyl-hept-4-enyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: DMSO; (COCl)2; NEt₃ / -78 - 20 °C

2: Bu₂BOTf; Et₃N

3: 2,6-lutidine

4: LiBH₄ / methanol; diethyl ether

5: DMAP; Et₃N

6: OsO₄; NMO

7: aq. NaIO₄

8: 97 percent / toluene / 17 h / -78 °C

With 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; toluene; 1: Swern oxidation / 8: Roush crotylation;
DOI:10.1021/ja0289649