Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate

Base Information

Chemical Name:Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate
CAS No.:163275-36-3
Molecular Formula:C₄₄H₆₈O₈Si₂
Molecular Weight:781.19
Hs Code.:

Synonyms:Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate

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Chemical Property of Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate

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Technology Process of Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate

There total 15 articles about Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-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: 100.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 163275-35-2
Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate

: 163275-36-3
Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

: 139400-25-2
(Z)-2-benzyloxy-1-methoxy-1-(trimethylsiloxy)ethene

: 163275-36-3
Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / MgBr₂*Et₂O / toluene / 1 h / -19 °C

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; magnesium bromide; In dichloromethane; toluene;
DOI:10.1246/bcsj.74.113

Reference yield:

: 60856-63-5
(2R)-(-)-3,3-dimethylbutane-1,2,4-triol

: 163275-36-3
Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

1.2: 92 percent / Et₃N / CH₂Cl₂

2.1: 21.2 g / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

3.1: 86 percent / n-BuLi / hexane; tetrahydrofuran / -15 - 20 °C

4.1: OsO₄; N-methylmorpholine-N-oxide / H₂O; acetone; 2-methyl-propan-2-ol / 72 h / 2 °C

5.1: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

6.1: 96 percent / NaH / tetrahydrofuran; dimethylformamide / 18 h / 0 - 20 °C

7.1: 85 percent / BH₃*Me₂S / toluene / 0.5 h / Heating

8.1: 67 percent / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

9.1: 87 percent / MgBr₂*Et₂O / toluene / 1 h / -19 °C

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; magnesium bromide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 2.1: Swern's oxidation / 3.1: Wittig reaction / 8.1: Swern's oxidation;
DOI:10.1246/bcsj.74.113