(2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine

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Chemical Name:(2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine
CAS No.:474799-98-9
Molecular Formula:C₄₆H₅₅NO₈
Molecular Weight:749.945
Hs Code.:

(2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine

Synonyms:(2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine

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Chemical Property of (2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine

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Technology Process of (2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine

There total 10 articles about (2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine 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: 76.0%

: (2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[(E)-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-vinyl]-pyrrolidine

: 474799-98-9
(2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine

Guidance literature:: With sodium acetate; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; at 85 ℃; for 5h;
DOI:10.1021/jo020252d

Reference yield:

: 298700-92-2
(2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[(E)-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-vinyl]-pyrrolidine

: 474799-98-9
(2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine

Guidance literature:: With sodium acetate; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; water; at 85 ℃; for 5h;
DOI:10.1016/S0040-4039(00)01005-4

Reference yield:

: 16838-89-4
2,3,5-tri-O-benzyl-D-ribofuranose

: 474799-98-9
(2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-2-benzyloxymethyl-5-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: 80 percent / 0.5 h / 110 °C

2.1: n-BuLi / hexane; diethyl ether / -78 - -70 °C

2.2: 72 percent / tetrahydrofuran; diethyl ether; hexane / 5 h / -70 °C

3.1: (AcO)2Cu*H₂O; Zn / acetic acid; H₂O / 0.75 h / 20 - 70 °C

4.1: 68 percent / 4 Angstroem molecular sieves; pyridine; Tf₂O / 0.5 h / 40 °C

5.1: 4 Angstroem molecular sieves; methyl triflate / acetonitrile / 0.5 h

5.2: NaBH₄ / methanol / 0.17 h / 20 °C

5.3: AgNO₃ / acetonitrile; H₂O / 0.17 h / 20 °C

6.1: 42 percent / 4 Angstroem molecular sieves; n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -30 °C

7.1: 76 percent / (p-toluenesulfonyl)hydrazide; AcONa / 1,2-dimethoxy-ethane / 5 h / 85 °C

With pyridine; n-butyllithium; trifluoromethylsulfonic anhydride; 4 A molecular sieve; copper diacetate; sodium acetate; toluene-4-sulfonic acid hydrazide; methyl trifluoromethanesulfonate; zinc; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; hexane; water; acetic acid; acetonitrile; 6.1: Wittig reaction;
DOI:10.1021/jo020252d