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[ CAS No. 5774-77-6 ]

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Chemical Structure| 5774-77-6
Chemical Structure| 5774-77-6
Structure of 5774-77-6 * Storage: {[proInfo.prStorage]}

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Alternatived Products of [ 5774-77-6 ]

Product Details of [ 5774-77-6 ]

CAS No. :5774-77-6 MDL No. :MFCD11643255
Formula : C9H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :165.19 g/mol Pubchem ID :-
Synonyms :

Safety of [ 5774-77-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5774-77-6 ]

  • Downstream synthetic route of [ 5774-77-6 ]

[ 5774-77-6 ] Synthesis Path-Downstream   1~15

  • 2
  • [ 32122-09-1 ]
  • [ 5774-77-6 ]
YieldReaction ConditionsOperation in experiment
94 - 96% With ammonium hydroxide; In dichloromethane; at 0℃; for 5h; Treatment of commercially available 1 (20g) with tert-butyldiphenylsilyl chloride (TBDPSCl) and imidazole in [THF/CH2C12] gave, after chromatographic purification, 2 (47.3 g, [80%).] This compound was characterized by 1H NMR. and MS. Oxidation of 2 (21.8g and 25g) using sodium chlorite gave 3 [(50G] total, quantitative yield). The product was characterized by 1H and [13C] NMR, and by MS. Benzyl alcohol [(50G)] on treatment with NaH (1.2 equiv) and ethyl bromoacetate (1 equiv) in THF gave 4a (32g, 36%), which was characterized by both [LHNMR,] and by MS. Scale up of this reaction yielded 100g of 4a. Reaction [OF 4A (5G)] with NH40H at [0 FOR] 5 h in [CH2C12] gave amide 4b (4.3g, 96%), which was characterized by 1H NMR and MS. A repeat of this experiment on 45 g [OF 4A] gave 38 g (94%) [OF 4B.] Dehydration of 4b (4.2 g) using [POC13] in acetonitrile gave 5 (1.75 g, 47%), which was characterized by 1H NMR, [13C] NMR and MS. A repeat of this experiment on 38g of 4b gave an additional 15.75 g (47%) of 5. Coupling of 5 (5 g) and phloroglucinol in MTBE with [HC1] gas bubbling at [0C] for 3 h gave 6 (2.6 g, 56%), which was characterized [BY IH] NMR, 13C NMR and MS. Selective protection of 6 (0.5 g) using TBDPSCI (2.5 equiv) and Et3N (2.5 equiv) in [CH2C12] at room temperature for 16 h gave 7 (1.2 g, 85%), which was characterized [BY LH] NMR and MS. Scale-up of this experiment on 2 g of 6 gave an additional 3.4 [G] [(62%)] of 7. Condensation of 7 (1.4 g) with 3 (1.35 equiv) in [CH2C12] [EDCI (1.5 equiv), DMAP (0. [35] equiv), [TSOH] (0. [35] equiv. ] at room temperature for 24 h gave 8 (1.5 g, 72%), which was characterized by 1H NMR. Scale up gave 35g of purified 8. Compound 8 (6g) was debenzylated using Rh/C as a catalyst (H2, 60 psi, EtOAc, rt, 24h) to give 8a (1.8g, 33%) along with 2.9g (53%) of the trans-esterified (migration of benzoyl group [RI)] product 8b. Both the intermediates 8a and 8b were characterized by 1H NMR
86% With ammonia; In methanol; at 25℃; for 5h; Into a 250-mL round-bottom flask, was placed 7 M H3(g)/MeOH (50 mL) and <strong>[32122-09-1]ethyl 2-(benzyloxy)acetate</strong> (15 g, 77.23 mmol, 1.00 equiv). The resulting solution was stirred for 5 h at room temperature (25 C) and then concentrated under vacuum. The crude product was recrystallized from 200 mL of PE/DCM (20/1) to afford 2-(benzyloxy)acetamide (11 g, 86%) as a white solid. MS: (ESI, m/z): 166[M+H]+
  • 4
  • [ 50-00-0 ]
  • [ 143-33-9 ]
  • [ 100-44-7 ]
  • [ 5774-77-6 ]
  • 5
  • [ 5774-77-6 ]
  • 1-amino-2-benzyloxyethylene-1,1-bisphosphonic acid [ No CAS ]
  • 6
  • [ 53008-65-4 ]
  • [ 5774-77-6 ]
  • 3,4-di-O-benzyl-6-O-dimethylpropanoyl-D-glucal [ No CAS ]
  • methyl O-(2-(N-benzyloxyacetyl)amino-2-deoxy-3,4-di-O-benzyl-6-O-dimethylpropanoyl-β-D-glucopyranosyl)-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside [ No CAS ]
  • 7
  • [ 55628-54-1 ]
  • [ 5774-77-6 ]
  • [ 80-97-7 ]
  • (+)-3-dihydrocholesteryl 3,4,6-tri-O-benzyl-2-(N-2-benzyloxyacetyl)amino-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 8
  • [ 55628-54-1 ]
  • [ 5774-77-6 ]
  • 2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-O-2-N-(2-benzyloxyethan-1-yl-1-ylidene)-α-D-glucopyranose [ No CAS ]
  • 9
  • [ 5774-77-6 ]
  • [ 80-97-7 ]
  • 3,4-di-O-benzyl-6-O-dimethylpropanoyl-D-glucal [ No CAS ]
  • (+)-3-dihydrocholesteryl 3,4-di-O-benzyl-2-(N-2-benzyloxyacetyl)amino-2-deoxy-6-O-dimethylpropanoyl-β-D-glucopyranoside [ No CAS ]
  • 10
  • [ 5774-77-6 ]
  • [ 530-93-8 ]
  • 2-benzyloxy-N-(3,4-dihydronaphthalen-2-yl)-acetamide [ No CAS ]
  • 11
  • [ 57224-63-2 ]
  • [ 5774-77-6 ]
  • Benzoic acid (2R,3S,4R)-3,4-bis-benzyloxy-3,4-dihydro-2H-pyran-2-ylmethyl ester [ No CAS ]
  • 3-O-(3,4-di-O-benzyl-6-O-benzoyl-2-(N-benzyloxyacetyl)amino-2-deoxy-β-D-glucopyranosyl)-N-benzyloxycarbonyl-L-threonine methyl ester [ No CAS ]
  • 12
  • [ 5774-77-6 ]
  • [ 536-38-9 ]
  • [ 951123-06-1 ]
YieldReaction ConditionsOperation in experiment
44% In N,N-dimethyl-formamide; at 130℃; for 6h; To a solution of 2-Benzyloxy-acetamide (1.40 g, 8.56 mmol) in 4 ml of DMF was added 2-Bromo-1-(4-chloro-phenyl)-ethanone (2.0 g, 8.56 mmol) and the reaction <n="132"/>mixture was heated at 13O0C for 6 h under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), water (25 mL) was added and extracted with ethyl acetate (3 x 50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (230-400 M, 10% EtOAc-Hexane) to get the desired product (1.1 g, 44%).
  • 13
  • [ 5774-77-6 ]
  • 1-benzyloxy-3-phenyl-acetone semicarbazone [ No CAS ]
  • 15
  • [ 5774-77-6 ]
  • [ 13620-31-0 ]
YieldReaction ConditionsOperation in experiment
47% With trichlorophosphate; In acetonitrile; Treatment of commercially available 1 (20g) with tert-butyldiphenylsilyl chloride (TBDPSCl) and imidazole in [THF/CH2C12] gave, after chromatographic purification, 2 (47.3 g, [80%).] This compound was characterized by 1H NMR. and MS. Oxidation of 2 (21.8g and 25g) using sodium chlorite gave 3 [(50G] total, quantitative yield). The product was characterized by 1H and [13C] NMR, and by MS. Benzyl alcohol [(50G)] on treatment with NaH (1.2 equiv) and ethyl bromoacetate (1 equiv) in THF gave 4a (32g, 36%), which was characterized by both [LHNMR,] and by MS. Scale up of this reaction yielded 100g of 4a. Reaction [OF 4A (5G)] with NH40H at [0 FOR] 5 h in [CH2C12] gave amide 4b (4.3g, 96%), which was characterized by 1H NMR and MS. A repeat of this experiment on 45 g [OF 4A] gave 38 g (94%) [OF 4B.] Dehydration of 4b (4.2 g) using [POC13] in acetonitrile gave 5 (1.75 g, 47%), which was characterized by 1H NMR, [13C] NMR and MS. A repeat of this experiment on 38g of 4b gave an additional 15.75 g (47%) of 5. Coupling of 5 (5 g) and phloroglucinol in MTBE with [HC1] gas bubbling at [0C] for 3 h gave 6 (2.6 g, 56%), which was characterized [BY IH] NMR, 13C NMR and MS. Selective protection of 6 (0.5 g) using TBDPSCI (2.5 equiv) and Et3N (2.5 equiv) in [CH2C12] at room temperature for 16 h gave 7 (1.2 g, 85%), which was characterized [BY LH] NMR and MS. Scale-up of this experiment on 2 g of 6 gave an additional 3.4 [G] [(62%)] of 7. Condensation of 7 (1.4 g) with 3 (1.35 equiv) in [CH2C12] [EDCI (1.5 equiv), DMAP (0. [35] equiv), [TSOH] (0. [35] equiv. ] at room temperature for 24 h gave 8 (1.5 g, 72%), which was characterized by 1H NMR. Scale up gave 35g of purified 8. Compound 8 (6g) was debenzylated using Rh/C as a catalyst (H2, 60 psi, EtOAc, rt, 24h) to give 8a (1.8g, 33%) along with 2.9g (53%) of the trans-esterified (migration of benzoyl group [RI)] product 8b. Both the intermediates 8a and 8b were characterized by 1H NMR
Historical Records

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