methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-α-D-glucopyranoside
CAS No.:1569902-17-5
Molecular Formula:C₄₃H₅₄O₁₃
Molecular Weight:778.894
Hs Code.:

Synonyms:methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-α-D-glucopyranoside

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Chemical Property of methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-α-D-glucopyranoside

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Technology Process of methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-α-D-glucopyranoside

There total 10 articles about methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-α-D-glucopyranoside 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: 85.0%

: 1569902-14-2
methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranosyl)onate]-α-D-glucopyranoside

: 1569902-17-5
methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-α-D-glucopyranoside

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 120 ℃; for 1h;
DOI:10.1021/ol500275j

Reference yield:

: 31024-99-4,54187-72-3,76249-79-1
1,2-dideoxy-4,5:7,8-di-O-isopropylidene-D-erythro-D-manno-1-yno-octitol

: 1569902-17-5
methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide; silver nitrate / acetone / 0.5 h / 0 - 20 °C

3.1: magnesium sulfate; sodium hydrogencarbonate / water / 0.5 h / 20 °C

3.2: 4 h / 0 °C

4.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 10 h

5.1: dmap / acetonitrile / 0 °C

6.1: triethyl phosphite / 2.5 h / 120 °C

7.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane; acetonitrile / 3 h / -45 °C / Molecular sieve

8.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 1 h / 120 °C

With dmap; N-Bromosuccinimide; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; magnesium sulfate; silver nitrate; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; mineral oil;
DOI:10.1021/ol500275j

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3:5,6-di-O-isopropylidene-D-mannofuranose

: 1569902-17-5
methyl 2,3,4-tri-O-benzyl-6-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 19 h / -40 - 0 °C / Inert atmosphere

2.1: cesium fluoride / acetonitrile; water / 2 h / 0 - 20 °C

3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: N-Bromosuccinimide; silver nitrate / acetone / 0.5 h / 0 - 20 °C

5.1: magnesium sulfate; sodium hydrogencarbonate / water / 0.5 h / 20 °C

5.2: 4 h / 0 °C

6.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 10 h

7.1: dmap / acetonitrile / 0 °C

8.1: triethyl phosphite / 2.5 h / 120 °C

9.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane; acetonitrile / 3 h / -45 °C / Molecular sieve

10.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 1 h / 120 °C

With dmap; N-Bromosuccinimide; N-iodo-succinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; magnesium sulfate; silver nitrate; cesium fluoride; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; mineral oil;
DOI:10.1021/ol500275j