2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol

Base Information

Chemical Name:2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol
CAS No.:871838-35-6
Molecular Formula:C₅₈H₆₆O₁₁Si
Molecular Weight:967.241
Hs Code.:

Synonyms:2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol

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Chemical Property of 2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol

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Technology Process of 2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol

There total 7 articles about 2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol 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: 64.0%

: 931091-51-9
2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-10,11-O-isopropylidene-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol

: 871838-35-6
2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol

Guidance literature:: With hydrogenchloride; In methanol; diethyl ether; at 20 ℃; for 2.5h;
DOI:10.1002/ejoc.200600825

Reference yield:

: 931091-47-3
1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-2,6:8,12-dianhydro-10,11-O-isopropylidene-D-lyxo-D-gulo-D-manno-tridecitol

: 871838-35-6
2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / nBu₄Br; 2,4-dimethylbutene; aq. NaOH / 3 h / 65 °C

2: 64 percent / HCl / diethyl ether; methanol / 2.5 h / 20 °C

With hydrogenchloride; sodium hydroxide; 2-Methyl-1-pentene; tetrabutylammomium bromide; In methanol; diethyl ether;
DOI:10.1002/ejoc.200600825

Reference yield:

: 931091-59-7
tert-butyl-{6-[(4-methoxy-benzyloxy)-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl]-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy}-diphenyl-silane

: 871838-35-6
2,6:8,12-dianhydro-1,3,4,5-tetra-O-benzyl-13-O-tert-butyldiphenylsilyl-7,9-O-methylene-D-lyxo-D-gulo-D-manno-tridecitol

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / BH₃*Me₂S / tetrahydrofuran / 3 h / 20 °C

2: 98 percent / DMAP / ethyl acetate / 0.5 h

3: 77 percent / DDQ / CH₂Cl₂ / 2 h / 20 °C

4: 98 percent / NaOMe / methanol / 2 h / 20 °C

5: 83 percent / nBu₄Br; 2,4-dimethylbutene; aq. NaOH / 3 h / 65 °C

6: 64 percent / HCl / diethyl ether; methanol / 2.5 h / 20 °C

With hydrogenchloride; dmap; sodium hydroxide; 2-Methyl-1-pentene; dimethylsulfide borane complex; tetrabutylammomium bromide; sodium methylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.200600825