benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

Base Information

Chemical Name:benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate
CAS No.:1421868-60-1
Molecular Formula:C₆₁H₆₆O₁₀Si
Molecular Weight:987.275
Hs Code.:

Synonyms:benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

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Chemical Property of benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

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Technology Process of benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

There total 10 articles about benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate 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: 84.0%

: 1421868-59-8
1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosiduronic acid

: 100-51-6,185532-71-2
benzyl alcohol

: 1421868-60-1
benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

Guidance literature:: With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo302508e

Reference yield:

: 866454-44-6
(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-(4-methoxybenzyloxy)propanal

: 1421868-60-1
benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium tetrahydroborate / water; ethanol / 2 h / 0 °C

2: tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 144 h / 20 °C / Molecular sieve; Inert atmosphere

3: sodium methylate / methanol; dichloromethane

4: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; dichloromethane / 3 h / 20 °C

5: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 2 h / 20 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; sodium methylate; tetra-(n-butyl)ammonium iodide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 2,4,6-tri-tert-butylpyrimidine; In methanol; ethanol; dichloromethane; water;
DOI:10.1021/jo302508e

Reference yield:

: 1421868-56-5
1,6-di-O-(tert-butyldiphenylsilyl)-2,5-di-O-(4-methoxybenzyl)-D-mannitol

: 1421868-60-1
benzyl (1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

Guidance literature:: Multi-step reaction with 6 steps

1: sodium periodate / water; tetrahydrofuran / 3 h / 20 °C

2: sodium tetrahydroborate / water; ethanol / 2 h / 0 °C

3: tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 144 h / 20 °C / Molecular sieve; Inert atmosphere

4: sodium methylate / methanol; dichloromethane

5: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; dichloromethane / 3 h / 20 °C

6: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 2 h / 20 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; sodium periodate; [bis(acetoxy)iodo]benzene; sodium methylate; tetra-(n-butyl)ammonium iodide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;
DOI:10.1021/jo302508e