1,5-anhydro-3-<<(benzyloxy)methyl>amino>-3,N,4,O-carbonyl-2,3-dideoxy-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enopyranose

Base Information

Chemical Name:1,5-anhydro-3-<<(benzyloxy)methyl>amino>-3,N,4,O-carbonyl-2,3-dideoxy-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enopyranose
CAS No.:161277-42-5
Molecular Formula:C₂₃H₂₅NO₆
Molecular Weight:411.455
Hs Code.:

Synonyms:1,5-anhydro-3-<<(benzyloxy)methyl>amino>-3,N,4,O-carbonyl-2,3-dideoxy-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enopyranose

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1,5-anhydro-3-<<(benzyloxy)methyl>amino>-3,N,4,O-carbonyl-2,3-dideoxy-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enopyranose

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 1,5-anhydro-3-<<(benzyloxy)methyl>amino>-3,N,4,O-carbonyl-2,3-dideoxy-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enopyranose

There total 7 articles about 1,5-anhydro-3-<<(benzyloxy)methyl>amino>-3,N,4,O-carbonyl-2,3-dideoxy-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enopyranose 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:

: 137915-37-8
1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

: 161277-42-5
1,5-anhydro-3-<<(benzyloxy)methyl>amino>-3,N,4,O-carbonyl-2,3-dideoxy-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, RT, overnight

2: BF₃*Et₂O / CH₂Cl₂ / 5 h / -78 °C

3: 80 percent / TsOH*H₂O, Py / H₂O / 14 h / 80 °C

4: 97 percent / NaH / CH₂Cl₂ / Ambient temperature

5: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) DMF, 30 min, 2.) DMF, 40 deg C, 10 h

6: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

7: 1.) NaH / 1.) DMF, from 0 deg C to RT, 20 min, 2.) DMF, RT, 4 h

With pyridine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja952907g

Reference yield:

: 148302-24-3
3-amino-1,5-anhydro-2,3-dideoxy-3,O,4,N-<(trichloromethyl)oxazolino>-6-O-(triisopropylsilyl)-D-ribo-hex-1-enopyranose

: 161277-42-5
1,5-anhydro-3-<<(benzyloxy)methyl>amino>-3,N,4,O-carbonyl-2,3-dideoxy-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / TsOH*H₂O, Py / H₂O / 14 h / 80 °C

2: 97 percent / NaH / CH₂Cl₂ / Ambient temperature

3: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) DMF, 30 min, 2.) DMF, 40 deg C, 10 h

4: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

5: 1.) NaH / 1.) DMF, from 0 deg C to RT, 20 min, 2.) DMF, RT, 4 h

With pyridine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja952907g

Reference yield:

: 148302-25-4
1,5-anhydro-2,3-dideoxy-3-(trichloroacetamido)-6-O-(triisopropylsilyl)-D-ribo-hex-1-enopyranose

: 161277-42-5
1,5-anhydro-3-<<(benzyloxy)methyl>amino>-3,N,4,O-carbonyl-2,3-dideoxy-6-O-(4-methoxybenzyl)-D-ribo-hex-1-enopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / NaH / CH₂Cl₂ / Ambient temperature

2: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) DMF, 30 min, 2.) DMF, 40 deg C, 10 h

3: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h

4: 1.) NaH / 1.) DMF, from 0 deg C to RT, 20 min, 2.) DMF, RT, 4 h

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja952907g