Allopyranoside, methyl 3-amino-3-deoxy

Allonic acid, 5-amino-5-deoxy-DL-, 139 Allopyranoside, methyl 2-acetamido-4,6-0-benzylidene-2-deoxy-3-0-(methyl-sulfonyl)-a-D-, infrared spectrum, 255 —, methyl 2-acetamido-2-deoxy-3-0-... 

Alginic acid, 279, 281, 286, 314, 322 esters of, 279, 314 salts of, 275, 279, 280, 286 Allopyranoside, methyl 2-acetamido-2-deoxy-a-D-, 3-methyl ethers, 202 Allose, 2-amino-2-deoxy-D-, methyl ethers of, 202, 214... 

As might be expected, the nitrous acid deamination of methyl 2-amino-4,6-0-benzylidene-2-deoxy-a-D-altropyranoside (10) hydrochloride leads45,46 uniquely to methyl 2,3-anhydro-4,6-0-benzylidene-a-D-allopyranoside (11). The benzylidene group does not play an... 

Methyl ethers of 2-amino-2-deoxy-D-allose have been prepared in order to be subsequently degraded into methyl ethers of n-ribose. Methylation of methyl 2-acetamido-4,6-0-benzylidene-2-deoxy-o -D-alloside gave the 3-methyl ether, which, in turn, was hydrolyzed to afford methyl 2-acetamido-2-deoxy-3-0-methyl-a-D-allopyranoside. After partial methylation, a dimethyl ether, probably the 3,6, was isolated, whereas exhaustive methylation afforded the 3,4,6-trimethyl ether. An identical trimethyl ether was isolated after methylation of methyl 2-acetamido-3,4,6-tri-0-acetyl-2-deoxy-a-n-alloside. Hydrolysis of the methyl glycosides of both the 3-methyl and the 3,4,6-trimethyl ethers gave crystalline hydrochlorides, and the base of the former ether was characterized by means of its crystalline Schiff base with 2-hydroxynaphthaldehyde. 

Me glycoside Methyl 3-amino-3-deoxy-a-D-allopyranoside C7H15NO5 193.199 Extremely hygroscopic cryst. (EtOH/ Et20) (as hydrochloride). [a]o -1-103.3 (c, 2 in D2O). 

Me glycoside Methyl S-amino-S-deoxy-fS-D-allopyranoside C7H15NO5 193.199 Mp 199-200°. 

Methyl 2-acetamido-5-amino-2,5-dideoxy-p-D-glucofuranoside, D-431 Methyl 2-acetamido-6-amino-2,6-dideoxy-p-D-idopyranoside, D-442 Methyl 2-acetamido-3,6-anhydro-2-deoxy-a-D-glucopyranoside, M-144 Methyl 4-acetamido-2,3-anhydro-4,6-dideoxy-a-D-allopyranoside, A-365 Methyl 2-acetamido-4-0-benzoyl-2-deoxy-3,6-di-0-methyl-a-D-glucopyranoside, M-145... 

Methyl 5-amino-l,3-0-benzylidene-5-deoxy-a-L-sorbopyranoside, A-336 Methyl 3-amino-3-deoxy-p-D-allofuranoside, A-157 Methyl 3-amino-3-deoxy-a-D-allopyranoside, A-157 Methyl 3-amino-3-deoxy-p-D-allopyranoside, A-157 Methyl 3-amino-3-deoxy-D-alluronate, A-160 Methyl 3-amino-3-deoxy-a-D-altropyranoside, A-165 Methyl 2-amino-2-deoxy-a-D-arabinopyranoside, A-178 Methyl 2-amino-2-deoxy-p-D-arabinopyranoside, A-178 Methyl 4-amino-4-deoxy-a-D-arabinopyranoside, A-179 Methyl 4-amino-4-deoxy-a-L-arabinopyranoside, A-179 Methyl 4-amino-4-deoxy-p-L-arabinopyranoside, A-179 Methyl 2-amino-2-deoxy-4,6-0-ethylidene-3-0-inethyl-a-D-glucopyranoside, M-150... 

Methyl 3-acetamido-3-deoxy-a-D-allofnranoside, A-157 Methyl 3-acetamido-3-deoxy-p-D-allofnranoside, A-157 Methyl 4-acetamido-4,6-dideoxy-a-D-allopyranoside, A-365 Methyl 4-acetamido-4,6-dideoxy-p-D-allopyranoside, A-365 Methyl 3-acetamido-2,5,6-tri-0-acetyl-3-deoxy-p-D-allofuranoside, A-157 Methyl 3-acetamido-2,4,6-tri-0-acetyl-3-deoxy-a-D-allopyranoside, A-157 Methyl 3-acetamido-2,4,6-tri-0-acetyl-3-deoxy-p-D-allopyranoside, A-157 Methyl 2-0-acetyl-4,6-0-benzylidene-a-D-allopyranoside, M-155 Methyl 2-0-acetyl-4,6-0-(J )-benzylidene-3-chloro-3-deoxy-p-D-allopyranoside, C-71 Methyl a-D-allofuranoside, M-148 Methyl p-D-allofuranoside, M-148 Methyl a-D-allopyranoside, M-148 Methyl p-D-allopyranoside, M-148 Methyl 3-amino-3-deoxy-p-D-allofnranoside, A-157 Methyl 3-amino-3-deoxy-a-D-allopyranoside, A-157 Methyl 3-amino-3-deoxy-p-D-allopyranoside, A-157 Methyl 4-amino-4,6-dideoxy-a-D-allopyranoside, A-365 Methyl 4-amino-4,6-dideoxy-p-D-allopyranoside, A-365 Methyl 5,6-anhydro-2,3-0-isopropylidene-p-L-allofuranoside, M-148 Methyl 2-0-benzoyl-4,6-0-benzylidene-a-D-allopyranoside, M-155 Methyl 6-O-benzoyl-3,4-O -isopropylidene-2-O-tosyl-a-D-allopyranoside, M-148... 

With educts containing an axially oriented LG at C-3, in addition to an intramolecular Sn2 reaction with an axially oriented hydroxy or acetamido group in a vicinal position (IS, Table 3, entries 1 [26] and 2 [30]), elimination and/or hydride shift (E or M/E, entries 3 [30],4 [31] and 6 [32]), as well as substitution with retention of configuration (AS, entries 7 and 8 [27b]) have been observed. For the transformation outhned in entry 4, 2,6-di-ferf-butyl-4-methylpyridine was used as acid scavenger, since pyridine per se in a similar reaction had caused Sn2 displacement (entry 5 [33]). Of special interest are the results from the deamination of methyl 3-amino-3-deoxy-/5-D-allopyranoside (entry 6), where the main reaction consists of direct Sn2 displacement with formation of methyl... 

Methylation of methyl 3,4-anhydro-a-DL-talopyranoside, followed by acid-catalysed opening of the oxiran ring, has been used in a synthesis of methyl 2,6-di-O-methyl-a-DL-mannopyranoside (methyl oL-curamicoside). Ringopening of methyl 3,4-anhydro-6-0-trityI-DL-allopyranoside with ammonia etc., afforded derivatives of OL-kanosamine (3-amino-3-deoxy-DL-glucose). 

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