(2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanoic acid methoxy-methyl-amide

Base Information

Chemical Name:(2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanoic acid methoxy-methyl-amide
CAS No.:815600-29-4
Molecular Formula:C₂₄H₄₃NO₆Si
Molecular Weight:469.694
Hs Code.:

Synonyms:(2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanoic acid methoxy-methyl-amide

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Chemical Property of (2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanoic acid methoxy-methyl-amide

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Technology Process of (2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanoic acid methoxy-methyl-amide

There total 5 articles about (2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanoic acid methoxy-methyl-amide 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: 48.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 815600-28-3
(2S,3R,5R)-5-(t-butyldimethylsilyloxy)-3-hydroxy-N,6-dimethoxy-N,2-dimethylhexanamide

: 815600-29-4
(2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanoic acid methoxy-methyl-amide

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 35 ℃; for 48h;
DOI:10.1016/j.tetlet.2004.09.177

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 815600-29-4
(2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 276248-87-4
(R)-1-Methoxy-4-(4-methoxy-benzyloxy)-butan-2-ol

: 815600-29-4
(2S,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-3-(4-methoxy-benzyloxy)-2-methyl-hexanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 6 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

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