6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

Base Information

Chemical Name:6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol
CAS No.:896136-24-6
Molecular Formula:C₅₉H₆₁Cl₅O₁₀Si
Molecular Weight:1135.48
Hs Code.:

6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

Synonyms:6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

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Chemical Property of 6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

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Technology Process of 6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

There total 5 articles about 6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol 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: 72.0%

: (3R,4S,5R,6R)-5-[(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-(4-chloro-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-3,4-bis-(4-chloro-benzyloxy)-6-(4-chloro-benzyloxymethyl)-2-trimethylsilanylethynyl-tetrahydro-pyran-2-ol

: 896136-24-6
6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at -40 - -10 ℃;
DOI:10.1002/hlca.200690068

Reference yield:

: 896136-22-4
4,6-O-benzylidene-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->4)-2,3,6-tris-O-(4-chlorobenzyl)-D-glucono-1,5-lactone

: 896136-24-6
6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 20.9 g / hexane; tetrahydrofuran / 4 h / -78 °C

2.1: 72 percent / BF₃*Et₂O; Et₃SiH / acetonitrile; CH₂Cl₂ / -40 - -10 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1002/hlca.200690068

Reference yield:

: 4,6-O-benzylidene-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->4)-2,3,6-tris-O-(4-chlorobenzyl)-D-glucopyranose

: 896136-24-6
6-O-benzyl-2,3-bis-O-(4-chlorobenzyl)-β-D-glucopyranosyl-(1->6)-3,7-anhydro-4,5,8-tris-O-(4-chlorobenzyl)-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / DMSO; Ac₂O / 6 h / 26 °C

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

2.2: 20.9 g / hexane; tetrahydrofuran / 4 h / -78 °C

3.1: 72 percent / BF₃*Et₂O; Et₃SiH / acetonitrile; CH₂Cl₂ / -40 - -10 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; acetic anhydride; dimethyl sulfoxide; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1002/hlca.200690068