76101-14-9

Usage

Uses

Used in Organic Synthesis:
Methyl 2-Deoxy-2-N-phthalimido-b-D-glucopyranoside is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for the formation of diverse chemical bonds and reactions, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2-Deoxy-2-N-phthalimido-b-D-glucopyranoside is used as a starting material for the synthesis of various drug candidates. Its unique structure and reactivity enable the development of novel therapeutic agents with potential applications in the treatment of various diseases and medical conditions.
Used in Research and Development:
Methyl 2-Deoxy-2-N-phthalimido-b-D-glucopyranoside is also used in research and development settings to explore new synthetic routes and methodologies. Its unique properties and reactivity make it an attractive candidate for the development of innovative synthetic strategies and the discovery of new chemical entities with potential applications in various fields.

InChI:InChI=1/C15H17NO7/c1-22-15-10(12(19)11(18)9(6-17)23-15)16-13(20)7-4-2-3-5-8(7)14(16)21/h2-5,9-12,15,17-19H,6H2,1H3

Upstream product

• 67-56-1 methanol 
• 70831-94-6 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide 
• 136810-00-9 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-seleno-β-D-glucopyranoside 
• 10028-45-2 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 85-44-9 phthalic anhydride 
• 7772-87-4 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 31505-45-0 2-deoxy-2-phthalimido-D-glucopyranose 
• 76101-13-8 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 

Downstream Products

• 97276-95-4 methyl 4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 
• 81927-56-2 methyl 4,6-O-benzylidene-2-deoxy-2-phthalimide-β-D-glucopyranoside 
• 86263-38-9 Methyl 3,6-Di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 111730-31-5 methyl 3-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 97242-79-0 methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 
• 97276-96-5 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 278784-86-4 methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 278784-84-2 methyl (3,4,6-tri-O-acetyl-2-deoxy-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 204766-30-3 methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 97242-77-8 methyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 81927-58-4 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 97242-82-5 methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside 
• 97242-88-1 methyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 97242-81-4 methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

Regio/Stereoselective Glycosylation of Diol and Polyol Acceptors in Efficient Synthesis of Neu5Ac-α-2,3-LacNPhth Trisaccharide

A concise approach to a Neu5Ac-α-2,3-LacNPhth trisaccharide derivative was developed. First, the regio/stereoselective glycosylation between glycoside donors and glucoNPhth diol acceptors was investigated. It was found that the regioselectivity depends not only on the steric hindrance of the C2-NPhth group and the C6-OH protecting group of the glucosamine acceptors, but also on the leaving group and protecting group of the glycoside donors. Under optimized conditions, LacNPhth derivatives were synthesized in up to 92 % yield through a regio/stereoselective glycosylation between peracetylated-α-galactopyranosyl trichloroacetimidate and p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-d-glucopyranoside, avoiding the formation of glycosylated orthoesters and anomeric aglycon transfer. Then, the LacNPhth derivative was deacylated and then protected on the primary position by TBDPS to form a LacNPhth polyol acceptor. Finally, the Neu5Ac-α-2,3-LacNPhth derivative was synthesized in 48 % yield through the regio/stereoselective glycosylation between the LacNPhth polyol acceptor and a sialyl phosphite donor. Starting from d-glucosamine hydrochloride, the target Neu5Ac-α-2,3-LacNPhth derivative was synthesized in a total yield of 18.5 % over only 10 steps.

SYNTHETIC OLIGOGLUCOSAMINES FOR IMPROVEMENT OF PLANT GROWTH AND YIELD

The disclosure provides formulations comprising synthetic oligoglucosamines and methods for improving plant growth and crop yield therewith. These formulations may be applied to propagating materials, including seeds and other regenerable plant parts, including cuttings, bulbs, rhizomes and tubers. They may also be applied to foliage, or soil either prior to or following planting of propagating materials. Such applications may be made alone or in combination with fungicides, insecticides, nematicides and other agricultural agents used to improve plant growth and crop yield.

SYNTHETIC SALT COMPLEXES FOR IMPROVEMENT OF PLANT GROWTH AND YIELD

The disclosure provides agricultural compositions comprising oligoglucosamine salt complexes and methods for improving plant growth and crop yield. These compositions may be applied to plant propagating materials, including seeds and other regenerable plant parts, including cuttings, bulbs, rhizomes and tubers. They may also be applied to foliage, or soil either prior to or following planting of plant propagating materials. Such applications may be made alone or in combination with fungicides, insecticides, nematicides and other agricultural agents used to improve plant growth and crop yield.

USE OF GLUCOSAMINE AMIDES AS PLANT GROWTH AND YIELD ENHANCERS

The invention provides compositions and methods for improving plant growth and crop yield. More specifically, the present invention relates to compositions comprising the glucosamine amide N-palmitoleyl-D-glucosamine (NPG) and other substituted glucosamine compounds. NPG and its substituted analogs may be applied to plant propagating materials, including seeds and other regenerable plant parts, including cuttings, bulbs, rhizomes and tubers. NPG and its analogs may also be applied to foliage or soil either prior to or following planting of plant propagating materials. Such applications may be made alone or in combination with fungicides, insecticides, nematicides and other agricultural agents used to improve plant growth and crop yield. NPG and its analogs can improve the agronomic performance of a variety of crops including barley, canola, corn, potato, soybean and wheat.

PROCESSES FOR CHEMICAL SYNTHESIS OF LIPOCHITOOLIGOSACCHARIDES

Processes for the synthesis of lipochitooligosaccharides were developed. A fully acylated oligoglucosamine precursor is prepared and reacted with a glucosamine monomer that has an amine protecting phthaloyl group. With removal of the phthaloyl group, a fatty acid may be added on the terminal glucosamine unit, forming a lipochitooligosaccharide. The processes can be adapted for use on a commercial scale.

Low molecular weight polyglucosamines and polygalactosamines

Compositions containing enriched populations of beta linked low molecular weight polymers of galactosamine and glucosamine are provided. The compositions are useful, for example, as antibacterial additives for food and other edible applications, as precursors for synthesizing other biologically active molecules related to chitin/chitosan oligomers, and/or as pharmaceutical compounds.

Conversion of glucosamine to galactosamine and allosamine derivatives: Control of inversions of stereochemistry at C-3 and C-4

The reactions of sodium benzoate with a series of trimesylates derived from glucosamine have been examined in an attempt to gain facile access to galactosamine analogues. Trimesylate 17, in which the amino group was protected as a phthalimide, underwent double displacement at positions 4 and 6 to give the dibenzoate 18 with the desired galactosamine configuration. In contrast, trimesylates 21 and 27, in which the amino groups were protected as acetamides, unexpectedly underwent double displacement at positions 3 and 6, giving products 22 and 28, respectively, with allosamine configurations.

Efficient Synthesis of 3,6-Dideoxy-β-D-arabino-hexopyranosyl-Terminated LacdiNac Glycan Chains of the Trichinella spiralis Parasite

The synthesis of a linear trisaccharide epitope of the Trichinella spiralis N-linked glycan, in a form amenable to glycoconjugate formation, is reported. The trisaccharide contains the synthetically challenging LacdiNAc [β-GalpNAc(1→4)-β-GlcpNAc] element,

APPLICATION OF PHENYL 1-SELENOGLYCOSIDES IN THE SYNTHESIS OF A CELL-WALL TETRAMERIC FRAGMENT OF PROTEUS VULGARIS STRAIN 5/43

DAST-assisted rearrangement of 3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl azide followed by treatment of the generated fluorides with ethanethiol and BF3*OEt2 gave glycosyl donor ethyl 3-O-allyl-2-azido-4-O-benzyl-2,6-dideoxy-1-thio-α/β-L-glucopyranoside.St

Synthesis of the 2"-hydroxy, 4"-deoxy and 4"-epi analogues of beta-D-GalNAc-(1-->3)-alpha-D-Gal-(1-->4)-beta-D-Gal, the terminal trisaccharide of globotetraose.

Radical deoxygenation of methyl 3,6-di-O-benzoyl-2-deoxy-4-O-imidazol-1-yl-thiocarbonyloxy-2-phtha limido-beta-D - glucopyranoside 5 gave methyl 3,6-di-O-benzoyl-2,4-dideoxy-2-phthalimido-beta-D-glucopyranoside 6, which was converted into the correspondin