5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl

Base Information

Chemical Name:5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl
CAS No.:377777-50-9
Molecular Formula:C₃₆H₃₄N₂O₄
Molecular Weight:558.677
Hs Code.:

Synonyms:5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl

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Chemical Property of 5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl

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Technology Process of 5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl

There total 4 articles about 5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl 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: 32.0%

: 14233-64-8,134307-32-7,55094-52-5
(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

: 160539-05-9
5-iodo-2,2'-bipyridine

: 377777-50-9
5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl

Guidance literature:: 5-iodo-2,2'-bipyridine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h;

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one; In tetrahydrofuran; at -78 - 20 ℃; for 16h;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 16h;
DOI:10.1002/1521-3773(20010817)40:16<3012::AID-ANIE3012>3.0.CO;2-Y

Reference yield:

: (3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-2-[2,2']bipyridinyl-5-yl-tetrahydro-furan-2-ol

: 377777-50-9
5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃;
DOI:10.1002/chem.200400858

Reference yield:

: 15862-19-8
5-bromo-2,2'-bipyridyl

: 377777-50-9
5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl

Guidance literature:: Multi-step reaction with 3 steps

1.1: 94 percent / CuI; NaI; rac-trans-N,N'-dimethyl-1,2-cyclohexanediamine / dioxane / 70 h / 110 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: tetrahydrofuran; hexane / 3 h / -78 °C

3.1: 3.51 g / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

With triethylsilane; copper(l) iodide; n-butyllithium; boron trifluoride diethyl etherate; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium iodide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane;
DOI:10.1002/chem.200400858