8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4)

Base Information

Chemical Name:8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4)
CAS No.:131755-66-3
Molecular Formula:C₃₅H₄₈O₈
Molecular Weight:596.761
Hs Code.:

Synonyms:8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4)

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Chemical Property of 8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4)

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Technology Process of 8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4)

There total 4 articles about 8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4) 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:

: 131755-65-2
3-O-Benzyl-2,4-dideoxy-2,4-di-C-methyl-D-allitol

: 131755-66-3
8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4)

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / conc. H₂SO₄ / acetone / 1 h / 0 °C

2: oxalyl chloride, DMSO, triethylamine / dimethylsulfoxide / 1.) -78 degC, 15 min

3: 1.) butyllithium / 1.) ether, hexane, -90 degC, 0.5 h, 2.) -90 degC, 0.5 h

With n-butyllithium; oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; triethylamine; In dimethyl sulfoxide; acetone;
DOI:10.1016/S0040-4020(01)85586-1

Reference yield:

: 105676-43-5,131831-44-2
3-O-Benzyl-2,4-dideoxy-5,6-O-isopropylidene-2,4-di-C-methyl-D-allitol

: 131755-66-3
8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4)

Guidance literature:: Multi-step reaction with 2 steps

1: oxalyl chloride, DMSO, triethylamine / dimethylsulfoxide / 1.) -78 degC, 15 min

2: 1.) butyllithium / 1.) ether, hexane, -90 degC, 0.5 h, 2.) -90 degC, 0.5 h

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dimethyl sulfoxide;
DOI:10.1016/S0040-4020(01)85586-1

Reference yield:

: 131755-63-0,131755-64-1
3-O-Benzyl-2,4-dideoxy-2,4-di-C-methyl-D-allopyranose

: 131755-66-3
8-O-Benzyl-3-C-(benzyloxymethyl)-3,5,7,9-tetradeoxy-1,2:10,11-di-O-isopropylidene-7,9-di-C-methyl-5-methylene-α-D-allo-L-talo-undecofuranose-(1,4)

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / LiAlH₄ / tetrahydrofuran / 2 h / 25 °C

2: 97 percent / conc. H₂SO₄ / acetone / 1 h / 0 °C

3: oxalyl chloride, DMSO, triethylamine / dimethylsulfoxide / 1.) -78 degC, 15 min

4: 1.) butyllithium / 1.) ether, hexane, -90 degC, 0.5 h, 2.) -90 degC, 0.5 h

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dimethyl sulfoxide; acetone;
DOI:10.1016/S0040-4020(01)85586-1