methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
CAS No.:271245-12-6
Molecular Formula:C₅₀H₅₈O₁₄S
Molecular Weight:915.068
Hs Code.:

Synonyms:methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

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Chemical Property of methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

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Technology Process of methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

There total 4 articles about methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-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: 94.0%

: 2397-26-4
N,N-dimethyl(chlorophenylmethylene)ammonium chloride

: 271245-11-5
methyl O-(methyl 4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

: 271245-12-6
methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: N,N-dimethyl(chlorophenylmethylene)ammonium chloride; methyl O-(methyl 4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside; With pyridine; In dichloromethane; at 20 ℃; for 24h;

With pyridine; hydrogen sulfide; In dichloromethane;
DOI:10.1016/S0957-4166(99)00557-1

Reference yield:

: methyl 3-O-benzoyl-4,5:7,8-di-O-isopropylidene-α,β-D-glycero-D-talo-2-octulopyranosonate

: 271245-12-6
methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / Huenig's base / acetonitrile / 1 h / 20 °C

2.1: 62 percent / TMSOTf / CH₂Cl₂ / 3 h / -15 °C

3.1: 90 percent / NaOMe / methanol / 24 h / 30 °C

4.1: pyridine / CH₂Cl₂ / 24 h / 20 °C

4.2: 94 percent / H₂S; pyridine / CH₂Cl₂

With pyridine; trimethylsilyl trifluoromethanesulfonate; sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile; 1.1: Substitution / 2.1: glycosidation / 3.1: debenzoylation / 4.1: Substitution / 4.2: sulfurylation;
DOI:10.1016/S0957-4166(99)00557-1

Reference yield:

: methyl 3-O-benzoyl-2-O-diethylphosphite-4,5:7,8-di-O-isopropylidene-α,β-D-glycero-D-talo-2-octulopyranosonate

: 271245-12-6
methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 62 percent / TMSOTf / CH₂Cl₂ / 3 h / -15 °C

2.1: 90 percent / NaOMe / methanol / 24 h / 30 °C

3.1: pyridine / CH₂Cl₂ / 24 h / 20 °C

3.2: 94 percent / H₂S; pyridine / CH₂Cl₂

With pyridine; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; dichloromethane; 1.1: glycosidation / 2.1: debenzoylation / 3.1: Substitution / 3.2: sulfurylation;
DOI:10.1016/S0957-4166(99)00557-1