(1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

Base Information

Chemical Name:(1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid
CAS No.:1574543-51-3
Molecular Formula:C₂₈H₃₆O₅Si
Molecular Weight:480.676
Hs Code.:

Synonyms:(1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

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Chemical Property of (1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

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Technology Process of (1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

There total 6 articles about (1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid 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:

: 1574543-69-3
C₃₁H₄₀O₅Si

: (1R,2R,3aS,6aR)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

: 1574543-51-3
(1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

Guidance literature:: With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 50 ℃; for 3h; Overall yield = 9.8 g;
DOI:10.1021/ol5002973

Reference yield:

: 1574543-68-2
C₁₃H₁₆O₄

: (1R,2R,3aS,6aR)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

: 1574543-51-3
(1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tris(acetoxy)borohydride / acetonitrile; acetic acid / 1 h / 0 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2.2: 12 h / 0 - 20 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / acetonitrile / 3 h / 50 °C

With pyrrolidine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetic acid; acetonitrile;
DOI:10.1021/ol5002973

Reference yield:

: 1574543-45-5
(R)-2-oxo-1-phenyl-2-(piperidin-1-yl)ethyl 4-(cyclopent-3-enyl)-3-oxobutanoate

: (1R,2R,3aS,6aR)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

: 1574543-51-3
(1S,2S,3aR,6aS)-1-(tert-butyldiphenylsilyloxy)methyl-2-methoxymethoxy-1,2,3,3a,4,6a-hexahydropentalene-1-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 4-acetamidobenzenesulfonyl azide / acetonitrile / 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) / dichloromethane / 8 h / 20 °C / Inert atmosphere

3.1: titanium(IV) isopropylate / 23 h / 60 °C / Inert atmosphere

4.1: formaldehyd; potassium hydrogencarbonate / water / 15 h / -25 °C / Inert atmosphere

5.1: sodium tris(acetoxy)borohydride / acetonitrile; acetic acid / 1 h / 0 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

6.2: 12 h / 0 - 20 °C / Inert atmosphere

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / acetonitrile / 3 h / 50 °C

With pyrrolidine; titanium(IV) isopropylate; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formaldehyd; dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); 4-acetamidobenzenesulfonyl azide; sodium tris(acetoxy)borohydride; potassium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; acetic acid; acetonitrile;
DOI:10.1021/ol5002973