methyl 2,4,6-tri-O-benzyl-3-O-[methyl (7,8-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-β-D-galactopyranoside

Base Information

Chemical Name:methyl 2,4,6-tri-O-benzyl-3-O-[methyl (7,8-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-β-D-galactopyranoside
CAS No.:1569902-32-4
Molecular Formula:C₄₀H₅₀O₁₃
Molecular Weight:738.829
Hs Code.:

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

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

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

There total 12 articles about methyl 2,4,6-tri-O-benzyl-3-O-[methyl (7,8-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-β-D-galactopyranoside 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:

: 1569902-34-6
C₃₇H₄₆O₁₃

: 77-76-9
2,2-dimethoxy-propane

: 1569902-32-4
methyl 2,4,6-tri-O-benzyl-3-O-[methyl (7,8-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-β-D-galactopyranoside

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4h; Inert atmosphere;
DOI:10.1021/ol500275j

Reference yield:

: 1569902-22-2
methyl 2,4,6-tri-O-benzyl-3-O-[methyl (4,5:7,8-di-O-isopropylidene-3-deoxy-3-iodo-D-glycero-β-D-galacto-2-octulopyranosyl)onate]-β-D-glactopyranoside

: 1569902-32-4
methyl 2,4,6-tri-O-benzyl-3-O-[methyl (7,8-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 2,2'-azobis(isobutyronitrile); triphenylstannane / toluene / 1 h / 120 °C

2: toluene-4-sulfonic acid / methanol / 10 h / 0 - 20 °C

3: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere

With 2,2'-azobis(isobutyronitrile); triphenylstannane; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide; toluene;
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

: 1569902-32-4
methyl 2,4,6-tri-O-benzyl-3-O-[methyl (7,8-O-isopropylidene-3-deoxy-β-D-manno-2-octulopyranosyl)onate]-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 10 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: 2,2'-azobis(isobutyronitrile); triphenylstannane / toluene / 1 h / 120 °C

9.1: toluene-4-sulfonic acid / methanol / 10 h / 0 - 20 °C

10.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere

With dmap; N-Bromosuccinimide; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; triphenylstannane; hydrogen; sodium hydride; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; silver nitrate; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;
DOI:10.1021/ol500275j