2,6-anhydro-3-deoxy-1-C-(quinoline-8-yl)-4,5,7-tris-O-(phenylmethyl)-D-arabino-hept-2-enose

Base Information

Chemical Name:2,6-anhydro-3-deoxy-1-C-(quinoline-8-yl)-4,5,7-tris-O-(phenylmethyl)-D-arabino-hept-2-enose
CAS No.:1353093-93-2
Molecular Formula:C₃₇H₃₃NO₅
Molecular Weight:571.673
Hs Code.:

Synonyms:2,6-anhydro-3-deoxy-1-C-(quinoline-8-yl)-4,5,7-tris-O-(phenylmethyl)-D-arabino-hept-2-enose

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Chemical Property of 2,6-anhydro-3-deoxy-1-C-(quinoline-8-yl)-4,5,7-tris-O-(phenylmethyl)-D-arabino-hept-2-enose

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Technology Process of 2,6-anhydro-3-deoxy-1-C-(quinoline-8-yl)-4,5,7-tris-O-(phenylmethyl)-D-arabino-hept-2-enose

There total 6 articles about 2,6-anhydro-3-deoxy-1-C-(quinoline-8-yl)-4,5,7-tris-O-(phenylmethyl)-D-arabino-hept-2-enose 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: 74.0%

: 38707-70-9
8-formylquinoline

: 117136-22-8
3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose

: 1353093-93-2
2,6-anhydro-3-deoxy-1-C-(quinoline-8-yl)-4,5,7-tris-O-(phenylmethyl)-D-arabino-hept-2-enose

Guidance literature:: With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; caesium carbonate; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/ol202959y

Reference yield:

: 572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

: 1353093-93-2
2,6-anhydro-3-deoxy-1-C-(quinoline-8-yl)-4,5,7-tris-O-(phenylmethyl)-D-arabino-hept-2-enose

Guidance literature:: Multi-step reaction with 5 steps

1: acetic acid; zinc / water / -20 - 0 °C / Inert atmosphere

2: methanol; sodium methylate / 20 °C / Inert atmosphere

3: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 60 °C / Inert atmosphere

4: nitric acid; acetic anhydride / -33 - 25 °C / Inert atmosphere

5: 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; caesium carbonate / dichloromethane / 24 h / 20 °C / Inert atmosphere

With methanol; nitric acid; sodium methylate; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; acetic anhydride; sodium hydride; caesium carbonate; acetic acid; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ol202959y

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-glucose pentaacetate

: 1353093-93-2
2,6-anhydro-3-deoxy-1-C-(quinoline-8-yl)-4,5,7-tris-O-(phenylmethyl)-D-arabino-hept-2-enose

Guidance literature:: Multi-step reaction with 6 steps

1: hydrogen bromide; acetic acid / 12 h / 20 °C / Inert atmosphere

2: acetic acid; zinc / water / -20 - 0 °C / Inert atmosphere

3: methanol; sodium methylate / 20 °C / Inert atmosphere

4: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 60 °C / Inert atmosphere

5: nitric acid; acetic anhydride / -33 - 25 °C / Inert atmosphere

6: 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; caesium carbonate / dichloromethane / 24 h / 20 °C / Inert atmosphere

With methanol; hydrogen bromide; nitric acid; sodium methylate; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; acetic anhydride; sodium hydride; caesium carbonate; acetic acid; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ol202959y