dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside
CAS No.:1198156-48-7
Molecular Formula:C₄₅H₆₃N₃O₁₅Si
Molecular Weight:914.092
Hs Code.:

dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside

Synonyms:dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside

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Chemical Property of dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside

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Technology Process of dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside

There total 6 articles about dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-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:

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: C₄₄H₆₁N₃O₁₅Si

: 1198156-48-7
dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: In tetrahydrofuran; diethyl ether; at 20 ℃;
DOI:10.1021/ja907358k

Reference yield:

: 1380175-61-0
C₂₇H₃₂O₇S

: 1198156-48-7
dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.25 h / 0 - 5 °C / Inert atmosphere; Molecular sieve

2: trifluoroacetic acid / water; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 0.75 h / 20 °C / Inert atmosphere

4: tetrahydrofuran / Inert atmosphere

With N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol303270v

Reference yield:

: 1198155-81-5
dimethylthexylsilyl 6-O-levulinoyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

: 1198156-48-7
dimethylthexylsilyl O-(methyl 2-O-levulinoyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.25 h / 0 - 5 °C / Inert atmosphere; Molecular sieve

2: trifluoroacetic acid / water; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; dichloromethane / 0.75 h / 20 °C / Inert atmosphere

4: tetrahydrofuran / Inert atmosphere

With N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol303270v