3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-β-D-ribofuranose

Base Information

Chemical Name:3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-β-D-ribofuranose
CAS No.:798552-99-5
Molecular Formula:C₂₄H₄₀Br₂O₄Si₂
Molecular Weight:608.558
Hs Code.:

Synonyms:3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-β-D-ribofuranose

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Chemical Property of 3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-β-D-ribofuranose

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Technology Process of 3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-β-D-ribofuranose

There total 3 articles about 3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-β-D-ribofuranose 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: 29.0%

: 169526-37-8
(6aR,9aS)-2,2,4,4-tetraisopropyltetrahydro-8H-furo[3,2-f ][1,3,5,2,4]trioxadisilocin-8-one

: 798552-96-2
2,4-dibromo-5-iodotoluene

: 798552-99-5
3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-β-D-ribofuranose

: 3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-α-D-ribofuranose

Guidance literature:: (6aR,9aS)-2,2,4,4-tetraisopropyltetrahydro-8H-furo[3,2-f ][1,3,5,2,4]trioxadisilocin-8-one; 2,4-dibromo-5-iodotoluene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 3h;
DOI:10.1021/ol048487u

Reference yield: 10.0%

: 798552-99-5
3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-β-D-ribofuranose

: 3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-α-D-ribofuranose

Guidance literature:

Reference yield:

: 625-95-6
3-Iodotoluene

: 798552-99-5
3',5'-O-((1,1,3,3-tetraisopropyl)disiloxane-1,3-diyl)-1',2'-dideoxy-1'-(2,4-dibromo-5-methylphenyl)-β-D-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: 33 percent / Fe; Br₂; glacial acetioc acid / 2 h / 60 °C

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

2.2: 29 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 3 h / -78 °C

With n-butyllithium; bromine; iron; acetic acid; In tetrahydrofuran; hexane;
DOI:10.1021/ol048487u