HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyldimethylsilyl chloride → Methyl 2-acetamido-2-deoxy-6-O-t-butyldimethylsilyl-beta-D-glucopyranoside
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | Methyl glucoside | HCID 76607 | — |
| Reactant | N-[(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]acetamide | HCID 445750 | — |
| Solvent | Imidazole | HCID 795 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 2-acetamido-2-deoxy-6-O-t-butyldimethylsilyl-beta-D-glucopyranoside | HCID 10760257 | — |
Reaction Steps
This compound was prepared from the corresponding methyl glucoside, Methyl 2-acetamido-2-deoxy-β-D-glucopyranoside (Carbohydrates, Ed. Collins, P. M., Chapman and Hall, New York, 1987, p. 414) by treatment with t-butyldimethylchlorosilane in DMF and imidazole. 1H NMR δ0.00 (2Xs, 6H), 0.80 (2Xs, 9H), 1.98 (s, br, 3H), 3.20-3.32 (m, 1H), 3.32-3.50 (s superimposed on m 5H), 3.59 (dd, J=12, 8, 1H), 3.76, 3.84 (ABX, JAB=18, 2H), 4.28 (d, J=8, 1H), 6.42 (d br J=4, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05481006 |
| Source dataset | uspto-grants-1996_01 |
| ORD ID | ord-4cc3ec1f2b6c4245857436aabebbea17 |
| Source note | uspto-grants-1996_01 |