thexyldimethylsilyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:thexyldimethylsilyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside
CAS No.:271245-17-1
Molecular Formula:C₄₅H₆₇NO₁₃Si
Molecular Weight:858.111
Hs Code.:

thexyldimethylsilyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Chemical Property of thexyldimethylsilyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Technology Process of thexyldimethylsilyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 6 articles about thexyldimethylsilyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-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:

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

: 271245-17-1
thexyldimethylsilyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

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

2.1: 56 percent / TMSOTf / CH₂Cl₂ / 3 h / -15 °C

3.1: 91 percent / NaOMe / methanol / 24 h / 30 °C

4.1: pyridine / CH₂Cl₂ / 24 h / 20 °C

4.2: 94 percent / H₂S; pyridine / CH₂Cl₂ / 0.08 h

5.1: Bu₃SnH; AIBN / toluene / 2 h / 90 °C

5.2: H₂S; pyridine / H₂O / 36 h / 20 °C

6.1: pyridine

With pyridine; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; toluene; acetonitrile; 1.1: Substitution / 2.1: glycosidation / 3.1: debenzoylation / 4.1: Substitution / 4.2: sulfurylation / 5.1: deoxygenation / 5.2: Reduction / 6.1: Acetylation;
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

: 271245-17-1
thexyldimethylsilyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 56 percent / TMSOTf / CH₂Cl₂ / 3 h / -15 °C

2.1: 91 percent / NaOMe / methanol / 24 h / 30 °C

3.1: pyridine / CH₂Cl₂ / 24 h / 20 °C

3.2: 94 percent / H₂S; pyridine / CH₂Cl₂ / 0.08 h

4.1: Bu₃SnH; AIBN / toluene / 2 h / 90 °C

4.2: H₂S; pyridine / H₂O / 36 h / 20 °C

5.1: pyridine

With pyridine; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; sodium methylate; In methanol; dichloromethane; toluene; 1.1: glycosidation / 2.1: debenzoylation / 3.1: Substitution / 3.2: sulfurylation / 4.1: deoxygenation / 4.2: Reduction / 5.1: Acetylation;
DOI:10.1016/S0957-4166(99)00557-1

Reference yield:

: 271245-15-9
thexyldimethylsilyl O-(methyl 4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

: 271245-17-1
thexyldimethylsilyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / CH₂Cl₂ / 24 h / 20 °C

1.2: 94 percent / H₂S; pyridine / CH₂Cl₂ / 0.08 h

2.1: Bu₃SnH; AIBN / toluene / 2 h / 90 °C

2.2: H₂S; pyridine / H₂O / 36 h / 20 °C

3.1: pyridine

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; toluene; 1.1: Substitution / 1.2: sulfurylation / 2.1: deoxygenation / 2.2: Reduction / 3.1: Acetylation;
DOI:10.1016/S0957-4166(99)00557-1