ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate

Base Information

Chemical Name:ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate
CAS No.:880883-31-8
Molecular Formula:C₃₈H₄₀O₇
Molecular Weight:608.731
Hs Code.:

Synonyms:ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate

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Chemical Property of ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate

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Technology Process of ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate

There total 10 articles about ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate 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: 85.0%

: ethyl 4,5,7,8-tetra-O-benzyl-3-deoxy-D-manno-2-octonate 1,3-propylene dithioketal

: 880883-31-8
ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; water; at -40 ℃; for 3h;
DOI:10.1002/anie.200503299

Reference yield:

: 2,3,6-tri-O-benzyl-4-O-p-methoxybenzyl-α-D-mannopyranose

: 880883-31-8
ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaBH₄ / tetrahydrofuran; ethanol / 3 h / 20 °C

2.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

3.1: aq. NaOH; tetra-n-butylammonium hydrogensulfate / tetrahydrofuran / 24 h / 20 °C

4.1: 8.11 g / camphorsulfonic acid / methanol; tetrahydrofuran / 6.5 h / 20 °C

5.1: 87 percent / imidazole; Ph₃P; I₂ / 0.25 h / 20 °C

6.1: NaH; tert-BuOH / dimethylformamide / 0 °C

6.2: dimethylformamide / 0.5 h / 20 °C

7.1: 1.40 g / DDQ / CH₂Cl₂; H₂O / 1 h / 0 °C

8.1: 85 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂; H₂O / 3 h / -40 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; iodine; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.200503299

Reference yield:

: 2,3,6-tri-O-benzyl-4-O-p-methoxybenzyl-D-mannitol

: 880883-31-8
ethyl (4,5,7,8-tetra-O-benzyl-2,3-dehydro-D-manno-2-octulopyranosyl)onate

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

2.1: aq. NaOH; tetra-n-butylammonium hydrogensulfate / tetrahydrofuran / 24 h / 20 °C

3.1: 8.11 g / camphorsulfonic acid / methanol; tetrahydrofuran / 6.5 h / 20 °C

4.1: 87 percent / imidazole; Ph₃P; I₂ / 0.25 h / 20 °C

5.1: NaH; tert-BuOH / dimethylformamide / 0 °C

5.2: dimethylformamide / 0.5 h / 20 °C

6.1: 1.40 g / DDQ / CH₂Cl₂; H₂O / 1 h / 0 °C

7.1: 85 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂; H₂O / 3 h / -40 °C

With pyridine; 1H-imidazole; sodium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; iodine; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.200503299