(2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one

Base Information

Chemical Name:(2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one
CAS No.:815600-30-7
Molecular Formula:C₃₉H₆₂O₉Si
Molecular Weight:703.001
Hs Code.:

(2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one

Synonyms:(2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one

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Chemical Property of (2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one

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Technology Process of (2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one

There total 15 articles about (2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one 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%

: 815600-19-2
1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propan-1-one

: 815600-20-5
(2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanal

: 815600-30-7
(2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one

Guidance literature:: With tin(II) trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; at -78 - 0 ℃; for 4h;
DOI:10.1016/j.tetlet.2004.09.177

Reference yield:

: 100-39-0
benzyl bromide

: 815600-30-7
(2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one

Guidance literature:: Multi-step reaction with 6 steps

1: NaH / dimethylformamide / 1 h / 25 °C

2: 94 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

3: Dess-Martin periodinane / CH₂Cl₂; pyridine / 18 h / 25 °C

4: tetrahydrofuran / 0.5 h / 25 °C

5: 75 percent / Dess-Martin periodinane / CH₂Cl₂; pyridine / 3 h / 25 °C

6: 80 percent / Sn(OTf)2; DIPEA / 4 h / -78 - 0 °C

With tin(II) trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; 3: Dess-Martin oxidation / 5: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2004.09.177

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 815600-30-7
(2R,3S,4R,5R,7R)-1-[(4R,5S)-5-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-octan-1-one

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole / CH₂Cl₂ / 18 h / 35 °C

2: DDQ / CH₂Cl₂; H₂O / 2 h / 25 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

4: 93 percent / n-Bu₂BOTf; Et₃N / CH₂Cl₂ / 2 h / 0 °C

5: 93 percent / AlMe₃ / CH₂Cl₂ / 16 h / 25 °C

6: 48 percent / CSA / CH₂Cl₂ / 48 h / 35 °C

7: 60 percent / DIBAL / toluene / 2 h / -78 °C

8: 80 percent / Sn(OTf)2; DIPEA / 4 h / -78 - 0 °C

With 1H-imidazole; tin(II) trifluoromethanesulfonate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; trimethylaluminum; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; toluene; 3: Swern oxidation;
DOI:10.1016/j.tetlet.2004.09.177