methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

Base Information

Chemical Name:methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside
CAS No.:132032-75-8
Molecular Formula:C₁₇H₂₂O₆
Molecular Weight:322.358
Hs Code.:

Synonyms:methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

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Chemical Property of methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

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Technology Process of methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

There total 4 articles about methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside 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:

: 82185-79-3
methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside

: 132032-75-8
methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Multistep reaction; 1.) THF, -60 deg C, 15 min; 2.) 5 min to r.t.;
DOI:10.1039/P19900003091

Reference yield:

: 100-39-0
benzyl bromide

: 132032-75-8
methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / NaH; HMPA; TBAI / tetrahydrofuran / 2 h / 23 °C

2: TBAF / tetrahydrofuran / 2 h / 23 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 23 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3: Swern oxidation;
DOI:10.1002/anie.200353478

Reference yield:

: 131089-35-5
methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

: 132032-75-8
methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-manno-hexodialdo-1,5-pyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / NaH; HMPA; TBAI / tetrahydrofuran / 2 h / 23 °C

2: TBAF / tetrahydrofuran / 2 h / 23 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 23 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3: Swern oxidation;
DOI:10.1002/anie.200353478