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

Base Information

• Chemical Name: thexyldimethylsilyl O-(methyl 3-O-acetyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 271245-19-3
• Molecular Formula: C₄₇H₆₉NO₁₅Si
• Molecular Weight: 916.148

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about thexyldimethylsilyl O-(methyl 3-O-acetyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-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 → thexyldimethylsilyl O-(methyl 3-O-acetyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (271245-19-3)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 56 percent / TMSOTf / CH₂Cl₂ / 3 h / -15 °C

3: 91 percent / NaOMe / methanol / 24 h / 30 °C

4: H₂S; pyridine / H₂O / 36 h

5: pyridine; DMAP / 12 h

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; hydrogen sulfide; sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; acetonitrile; 1: Substitution / 2: glycosidation / 3: debenzoylation / 4: Reduction / 5: 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 → thexyldimethylsilyl O-(methyl 3-O-acetyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (271245-19-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / TMSOTf / CH₂Cl₂ / 3 h / -15 °C

2: 91 percent / NaOMe / methanol / 24 h / 30 °C

3: H₂S; pyridine / H₂O / 36 h

4: pyridine; DMAP / 12 h

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; hydrogen sulfide; sodium methylate; In methanol; dichloromethane; water; 1: glycosidation / 2: debenzoylation / 3: Reduction / 4: Acetylation;

DOI:10.1016/S0957-4166(99)00557-1

Reference yield:

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 (271245-15-9) → thexyldimethylsilyl O-(methyl 3-O-acetyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (271245-19-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂S; pyridine / H₂O / 36 h

2: pyridine; DMAP / 12 h

With pyridine; dmap; hydrogen sulfide; In water; 1: Reduction / 2: Acetylation;

DOI:10.1016/S0957-4166(99)00557-1

upstream raw materials:

acetic anhydride

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

thexyldimethylsilyl O-(methyl 3-O-benzoyl-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

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