tetradecyl 2,3,4-tri-O-benzyl-6-O-[ethyl (4,5,7,8-tetra-O-benzyl-3-deoxy-3-iodo-α-D-manno-2-octulopyranosyl)onate]-β-D-glucopyranoside

Base Information

Chemical Name:tetradecyl 2,3,4-tri-O-benzyl-6-O-[ethyl (4,5,7,8-tetra-O-benzyl-3-deoxy-3-iodo-α-D-manno-2-octulopyranosyl)onate]-β-D-glucopyranoside
CAS No.:880883-35-2
Molecular Formula:C₇₉H₉₇IO₁₃
Molecular Weight:1381.54
Hs Code.:

Synonyms:tetradecyl 2,3,4-tri-O-benzyl-6-O-[ethyl (4,5,7,8-tetra-O-benzyl-3-deoxy-3-iodo-α-D-manno-2-octulopyranosyl)onate]-β-D-glucopyranoside

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Chemical Property of tetradecyl 2,3,4-tri-O-benzyl-6-O-[ethyl (4,5,7,8-tetra-O-benzyl-3-deoxy-3-iodo-α-D-manno-2-octulopyranosyl)onate]-β-D-glucopyranoside

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Technology Process of tetradecyl 2,3,4-tri-O-benzyl-6-O-[ethyl (4,5,7,8-tetra-O-benzyl-3-deoxy-3-iodo-α-D-manno-2-octulopyranosyl)onate]-β-D-glucopyranoside

There total 14 articles about tetradecyl 2,3,4-tri-O-benzyl-6-O-[ethyl (4,5,7,8-tetra-O-benzyl-3-deoxy-3-iodo-α-D-manno-2-octulopyranosyl)onate]-β-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: 93.0%

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

: 880883-32-9
tetradecyl 2,3,4-triO-benzyl-β-D-glucopyranoside

: 880883-35-2
tetradecyl 2,3,4-tri-O-benzyl-6-O-[ethyl (4,5,7,8-tetra-O-benzyl-3-deoxy-3-iodo-α-D-manno-2-octulopyranosyl)onate]-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -50 ℃;
DOI:10.1002/anie.200503299

Reference yield:

: 103279-23-8
tetradecyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

: 880883-35-2
tetradecyl 2,3,4-tri-O-benzyl-6-O-[ethyl (4,5,7,8-tetra-O-benzyl-3-deoxy-3-iodo-α-D-manno-2-octulopyranosyl)onate]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaOMe / methanol; tetrahydrofuran / 1 h / 20 °C

1.2: pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / 40 °C

1.3: NaH / dimethylformamide / 5 h / 50 °C

2.1: 3.51 g / CSA / methanol / 2 h / 40 °C

3.1: 93 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / -50 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; camphor-10-sulfonic acid; sodium methylate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/anie.200503299

Reference yield:

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

: 880883-35-2
tetradecyl 2,3,4-tri-O-benzyl-6-O-[ethyl (4,5,7,8-tetra-O-benzyl-3-deoxy-3-iodo-α-D-manno-2-octulopyranosyl)onate]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 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

8.1: 93 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / -50 °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