HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl 6-hydroxyhexanoate → 5-ethoxycarbonylpentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl 6-hydroxyhexanoate | HCID 357781 | — |
| Reactant | 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride | HCID 11100622 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | 5-ethoxycarbonylpentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside | HCID 54191059 | 74% |
Reaction Steps
Condensation of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride with 5-ethoxycarbonyl-1-pentanol under the same conditions as reported in example II gave a 74% yield of 5-ethoxycarbonylpentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside, mp 101°-102°, [α]D25 - 16.8° (c 1.06, chloroform). De-O-acetylation of this compound using sodium methoxide gave after crystallization a 92% yield of 4 mp 154°-155° (melts and resolidifies) remelts 167°, [α]D18 - 25.5° (c 1.1, water).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04137401 |
| Source dataset | uspto-grants-1979_01 |
| ORD ID | ord-d243872710e64186b509487da16b7c42 |
| Source note | uspto-grants-1979_01 |