76101-14-9

Basic information

• Product Name: Methyl 2-Deoxy-2-N-phthalimido-b-D-glucopyranoside
• Synonyms: Methyl2-deoxy-2-phthalimido-b-D-glucopyranoside;Methyl 2-Deoxy-2-N-phthalimido--D-glucopyranoside;Methyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-glucopyranoside;NSC 350991
• CAS NO: 76101-14-9
• Molecular Formula: C₁₅H₁₇NO₇
• Molecular Weight: 323.299
• Product Categories: Carbohydrates & Derivatives
• Mol File: 76101-14-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 553°C at 760 mmHg
• Flash Point: 288.2°C
• Appearance: /
• Density: 1.55g/cm³
• Vapor Pressure: 4.61E-13mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: Refrigerator
• CAS DataBase Reference: Methyl 2-Deoxy-2-N-phthalimido-b-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-Deoxy-2-N-phthalimido-b-D-glucopyranoside(76101-14-9)
• EPA Substance Registry System: Methyl 2-Deoxy-2-N-phthalimido-b-D-glucopyranoside(76101-14-9)

Safety Data

• Hazardous Substances Data: 76101-14-9(Hazardous Substances Data)

Usage

Uses

Methyl 2-Deoxy-2-N-phthalimido-β-D-glucopyranoside (cas# 76101-14-9) is a compound useful in organic synthesis.

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

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

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 
• 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 
• 129090-84-2 methyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 129090-85-3 methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 129090-87-5 2-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 
• 129090-86-4 2-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-6-allyloxymethyl-3,5-dihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 
• 129090-90-0 2-{(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl}-isoindole-1,3-dione 
• 129090-89-7 methyl 4-O-<3-O-allyl-4,6-O-(4-methoxybenzylidene)-β-D-galactopyranosyl>-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 100638-50-4 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 129090-88-6 C₄₃H₄₅F₆NO₁₆S₂ 

Relevant articles and documents

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 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.

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.