para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-α-D-glucopyranoside

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Chemical Name:para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-α-D-glucopyranoside
CAS No.:612841-80-2
Molecular Formula:C₂₇H₂₅NO₈
Molecular Weight:491.497
Hs Code.:

Synonyms:para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-α-D-glucopyranoside

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Chemical Property of para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-α-D-glucopyranoside

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Technology Process of para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-α-D-glucopyranoside

There total 11 articles about para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-α-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: 72.0%

: 100-02-7,78813-13-5,89830-32-0
4-nitro-phenol

: 612841-77-7
phenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-1-thio-β-D-glucopyranoside

: 612841-80-2
para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-α-D-glucopyranoside

: 612841-79-9
para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -30 ℃; for 0.5h;
DOI:10.1016/S0040-4039(03)01631-9

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 612841-80-2
para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 8.28 g / camphorsulphonic acid / dimethylformamide / 14 h / 20 °C

2.1: O₃ / CH₂Cl₂ / 0.03 h / -78 °C

2.2: Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

3.1: 858 mg / NaBH₄ / ethanol / 18 h / 20 °C

4.1: pyridine; DMAP / 22 h / 20 °C

5.1: 0.65 g / NaH / dimethylformamide / 18 h / 20 °C

6.1: 72 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; triflic acid / CH₂Cl₂ / 1 h / -40 °C

With pyridine; dmap; sodium tetrahydroborate; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; sodium hydride; ozone; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.009

Reference yield:

: (2R,3S,4S,5R,6S)-4-Benzyloxy-2-hydroxymethyl-6-phenylsulfanyl-2-vinyl-tetrahydro-pyran-3,5-diol

: 612841-80-2
para-nitrophenyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-methylene-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 8.28 g / camphorsulphonic acid / dimethylformamide / 14 h / 20 °C

2.1: O₃ / CH₂Cl₂ / 0.03 h / -78 °C

2.2: Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

3.1: 858 mg / NaBH₄ / ethanol / 18 h / 20 °C

4.1: pyridine; DMAP / 22 h / 20 °C

5.1: 0.65 g / NaH / dimethylformamide / 18 h / 20 °C

6.1: 72 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; triflic acid / CH₂Cl₂ / 1 h / -40 °C

With pyridine; dmap; sodium tetrahydroborate; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; sodium hydride; ozone; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.009