(1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine

Base Information

Chemical Name:(1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine
CAS No.:923592-16-9
Molecular Formula:C₃₃H₄₁NO₄
Molecular Weight:515.693
Hs Code.:

Synonyms:(1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine

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Chemical Property of (1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine

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Technology Process of (1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine

There total 12 articles about (1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine 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:

: 923592-15-8
(3S,4S,5S,6S,7S)-3,5,6-tris(benzyloxy)-8-tert-butoxyoctane-1,4,7-triyl tris(methanesulfonate)

: 923592-16-9
(1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine

Guidance literature:: With benzylamine; sodium iodide; In dimethyl sulfoxide; at 80 ℃; for 24h;
DOI:10.1021/ol062570v

Reference yield:

: 914638-64-5
(S)-4-(tert-butyldiphenylsilyloxy)-2-benzyloxy-1-butanal

: 923592-16-9
(1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine

Guidance literature:: Multi-step reaction with 9 steps

1.1: Chx₂BCl; triethylamine / diethyl ether / 1 h / 0 °C

1.2: diethyl ether / 5 h / 0 °C

1.3: 72 percent / phosphate buffer; H₂O₂ / diethyl ether; methanol; H₂O / 1 h / 20 °C / pH 7

2.1: 75 percent / 4-(dimethylamino)pyridine; i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

3.1: 80 percent / LiBH₄ / diethyl ether / 2 h / -90 °C

4.1: 82 percent Turnov_. / DDQ / tetrahydrofuran; H₂O / 24 h / 20 °C

5.1: 80 percent / NaH; TBAI / tetrahydrofuran / 0 - 40 °C

6.1: 77 percent / toluene; diethyl ether / 16 h / Heating

7.1: 97 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

8.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

9.1: 62 mg / benzylamine; NaI / dimethylsulfoxide / 24 h / 80 °C

With dmap; lithium borohydride; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; benzylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; 1.2: aldol addition;
DOI:10.1021/ol062570v

Reference yield:

: 914638-70-3
(S)-4-(tert-butyldiphenylsilyloxy)-2-benzyloxy-1-butanol

: 923592-16-9
(1R,2R,3R,7S,7aR)-1,2,7-tris(benzyloxy)-3-(tert-butoxymethyl)hexahydro-1H-pyrrolizine

Guidance literature:: Multi-step reaction with 10 steps

1.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

2.1: Chx₂BCl; triethylamine / diethyl ether / 1 h / 0 °C

2.2: diethyl ether / 5 h / 0 °C

2.3: 72 percent / phosphate buffer; H₂O₂ / diethyl ether; methanol; H₂O / 1 h / 20 °C / pH 7

3.1: 75 percent / 4-(dimethylamino)pyridine; i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

4.1: 80 percent / LiBH₄ / diethyl ether / 2 h / -90 °C

5.1: 82 percent Turnov_. / DDQ / tetrahydrofuran; H₂O / 24 h / 20 °C

6.1: 80 percent / NaH; TBAI / tetrahydrofuran / 0 - 40 °C

7.1: 77 percent / toluene; diethyl ether / 16 h / Heating

8.1: 97 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

9.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

10.1: 62 mg / benzylamine; NaI / dimethylsulfoxide / 24 h / 80 °C

With dmap; lithium borohydride; oxalyl dichloride; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; benzylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; 1.1: Swern oxidation / 2.2: aldol addition;
DOI:10.1021/ol062570v