3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Base Information

• Chemical Name: 3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol
• CAS No.: 863663-36-9
• Molecular Formula: C₃₄H₅₉NO₇Si
• Molecular Weight: 621.93
• Mol file: 863663-36-9.mol

Synonyms:3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Chemical Property of 3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

There total 2 articles about 3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(2R)-2-hydroxy-1,1-dimethylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol (863663-26-7) → 3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol (863663-36-9)

Guidance literature:

With pyridine; hydrogen fluoride; at 0 ℃; for 3h;

DOI:10.1002/anie.200500172

Reference yield:

3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-C-((2R)-2-{(4S,5R)-4-methyl-5-[(1Z)-1-methylbut-1-en-1-yl]-4,5-dihydroisoxazol-3-yl}propyl)-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol (863663-35-8) → 3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol (863663-36-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / (DHQD)2PHAL; K₃Fe(CN)6; K₂CO₃ / methanesulfonylamide; K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 3.5 h / 0 °C

2: 80 percent / HF; pyridine / 3 h / 0 °C

With pyridine; hydrogen fluoride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium osmate(VI); methanesulfonamide; In water; tert-butyl alcohol;

DOI:10.1002/anie.200500172

Reference yield:

3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol (863663-36-9) → erythronolide A (26754-37-0)

Guidance literature:

Multi-step reaction with 7 steps

1: TEMPO; KBr; aq. carbonate buffer / NaOCl / CH₂Cl₂ / 0.5 h / 0 °C / pH 8.6

2: 190 mg / 2-methyl-2-butene; NaClO₂; aq. citrate phosphate buffer / 2-methyl-propan-2-ol / 0.5 h / 0 °C / pH 3.8

3: Et₃N / tetrahydrofuran / 0 - 20 °C

4: 103 mg / Et₃N; DMAP / tetrahydrofuran; toluene / 0.75 h / 50 °C

5: 32 mg / Et₃N; HF*Et₃N / acetonitrile / 64 h / 30 °C

6: 93 percent / H₂; AcOH; Raney-Ni / ethanol / 0.33 h / 20 °C

7: 40 percent / Pd(OAc)2; H₂ / methanol; H₂O / 6 h / 20 °C

With dmap; palladium diacetate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; 2-methyl-but-2-ene; Carbonate buffer; citrate phosphate buffer; hydrogen; nickel; acetic acid; triethylamine hydrofluoride; triethylamine; potassium bromide; sodium hypochlorite; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1002/anie.200500172

upstream raw materials:

3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(2R)-2-hydroxy-1,1-dimethylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

3,5-O-benzylidene-7-O-[tert-butyl(dimethyl)silyl]-1,4,6-trideoxy-4,6-dimethyl-2-C-((2R)-2-{(4S,5R)-4-methyl-5-[(1Z)-1-methylbut-1-en-1-yl]-4,5-dihydroisoxazol-3-yl}propyl)-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Downstream raw materials:

(1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-2,9-dihydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one

(1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one

3,5-O-benzylidene-2,4,7-trideoxy-6-C-((2R)-2-{(4S,5R)-5-[(2R)-2-hydroxy-1,1-dimethylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-2,4-dimethyl-3,5-O-(1-methylethylidene)-6-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

erythronolide A

Refernces

• 1、 Muri, Dieter,Carreira, Erick M.. "Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studies". experimental part. p. 8695 - 8712. Retrieved 2010/01/15.