3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol

Base Information

• Chemical Name: 3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol
• CAS No.: 105544-92-1
• Molecular Formula: C₁₈H₂₈O₅
• Molecular Weight: 324.417
• Mol file: 105544-92-1.mol

Synonyms:3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol

Chemical Property of 3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol

There total 14 articles about 3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-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: 92.0%

3-O-benzyl-7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-4,5-O-isopropylidene-4-C-methyl-D-manno-heptitol (105544-91-0) → 3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol (105544-92-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)84382-8

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → 3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol (105544-92-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 73 percent / Mg / diethyl ether / 3.5 h / 23 °C

2: 1.) NaIO₄, 2.) LiAlH₄ / 1.) 24 deg C, 1 h, aqueous acetone, 2.) THF, 20 deg C, 20 min

3: 97 percent / imidazole / dimethylformamide / 2.66 h / 24 °C

4: pyridinium chlorochromate, molecular sieves 3 Angstroem / CH₂Cl₂ / 2 h / 22 °C

5: 85 percent / magnesium powder / tetrahydrofuran / 3 h / Ambient temperature

6: 1.) O₃, 2.) dimethyl sulfide / 1.) methylene dichloride, -78 deg C, 2.) room temperature

7: 88 percent / magnesium powder / diethyl ether / 1.5 h / 0 °C

8: 55 percent / NaH / tetrahydrofuran / 4 h / 21 °C

9: 95 percent / FeCl₃ / acetone / 1 h / 29 °C

10: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide; 3 A molecular sieve; tetrabutyl ammonium fluoride; iron(III) chloride; sodium hydride; ozone; magnesium; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1246/bcsj.62.2618

Reference yield:

(R)-1-((4R,5S)-5-((S)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol (4159-66-4,105617-51-4,107494-47-3,138127-63-6,138127-64-7) → 3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol (105544-92-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaIO₄, 2.) LiAlH₄ / 1.) 24 deg C, 1 h, aqueous acetone, 2.) THF, 20 deg C, 20 min

2: 97 percent / imidazole / dimethylformamide / 2.66 h / 24 °C

3: pyridinium chlorochromate, molecular sieves 3 Angstroem / CH₂Cl₂ / 2 h / 22 °C

4: 85 percent / magnesium powder / tetrahydrofuran / 3 h / Ambient temperature

5: 1.) O₃, 2.) dimethyl sulfide / 1.) methylene dichloride, -78 deg C, 2.) room temperature

6: 88 percent / magnesium powder / diethyl ether / 1.5 h / 0 °C

7: 55 percent / NaH / tetrahydrofuran / 4 h / 21 °C

8: 95 percent / FeCl₃ / acetone / 1 h / 29 °C

9: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide; 3 A molecular sieve; tetrabutyl ammonium fluoride; iron(III) chloride; sodium hydride; ozone; magnesium; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1246/bcsj.62.2618

upstream raw materials:

3-O-benzyl-7-O-(t-butyldiphenylsilyl)-1,2-dideoxy-4,5-O-isopropylidene-4-C-methyl-D-manno-heptitol

2,3-O-isopropylidene-D-ribofuranose

benzyl bromide

(S)-1-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

Downstream raw materials:

1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-ethanol

5-O-benzyl-1,6,7-trideoxy-3,4-O-isopropylidene-4-C-methyl-keto-D-arabino-2-heptulose

5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol

erythronolide A

Refernces

• 1、 Kinoshita, Mitsuhiro,Arai, Masayuki,Tomooka, Katsuhiko,Nakata, Masaya. "SYNTHETIC STUDIES OF ERYTHROMYCINS. II. ENANTIOSPECIFIC SYNTHESIS OF A C-10-C-13 SEGMENT OF ERYTHRONOLIDE A FROM D-RIBOSE". . p. 1811 - 1814. Retrieved 2007/10/02.