(7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-D-manno-heptitol

Base Information

• Chemical Name: (7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-D-manno-heptitol
• CAS No.: 250598-96-0
• Molecular Formula: C₂₆H₂₉NO₉
• Molecular Weight: 499.518
• Mol file: 250598-96-0.mol

Synonyms:(7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-D-manno-heptitol

Chemical Property of (7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-D-manno-heptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-D-manno-heptitol

There total 1 articles about (7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-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: 83.0%

(R)-[(3aR,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-phenyl-methanol (201863-41-4) + 4-nitro-benzoic acid (62-23-7) → (7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-D-manno-heptitol (250598-96-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 8h;

DOI:10.1016/S0968-0896(99)00164-9

Reference yield: 93.0%

(7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-D-manno-heptitol (250598-96-0) → (7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-D-glycero-D-manno-heptitol (201863-39-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1.5h;

DOI:10.1016/S0968-0896(99)00164-9

Reference yield:

(7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-7-O-(4-nitrobenzoyl)-D-glycero-D-manno-heptitol (250598-96-0) → (7S)-3,6-anhydro-2-deoxy-7-phenyl-D-altro-1,4-heptanolactone

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / NaOMe / methanol / 1.5 h / 20 °C

2: 96 percent / NaH / dimethylformamide / 0.5 h / 20 °C

3: 86 percent / 60 percent aq. AcOH / 8 h / 20 °C

4: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

5: 85 percent / NaI / butan-2-one / 12 h / Heating

6: 86 percent / 5 percent aq. H₂SO₄ / dioxane / 1 h / Heating

7: 85 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O / 3 h / 20 °C

8: 77 percent / PDC / CH₂Cl₂ / 1.5 h / Heating

9: 84 percent / H₂ / 10 percent Pd/C / ethyl acetate / 3 h / 760 Torr

With dipyridinium dichromate; sulfuric acid; hydrogen; oxygen; sodium methylate; sodium hydride; acetic acid; triethylamine; sodium iodide; copper(l) chloride; palladium dichloride; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; butanone; 1: Hydrolysis / 2: Alkylation / 3: Ring cleavage / 4: mesylation / 5: Elimination / 6: Ring cleavage / 7: Cyclization / 8: Oxidation / 9: Catalytic hydrogenation;

DOI:10.1016/S0968-0896(99)00164-9

upstream raw materials:

(R)-[(3aR,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-phenyl-methanol

4-nitro-benzoic acid

Downstream raw materials:

(7S)-3,6-anhydro-1,2:4,5-di-O-isopropylidene-7-C-phenyl-D-glycero-D-manno-heptitol

(7S)-3,6-anhydro-7-O-benzyl-1,2-dideoxy-7-C-phenyl-D-altro-hept-1-enitol

(7S)-3,6-anhydro-7-O-benzyl-1,2-dideoxy-4,5-O-isopropylidene-7-C-phenyl-D-altro-hept-1-enitol

(7S)-3,6-anhydro-7-O-benzyl-2-deoxy-7-C-phenyl-D-altro-1,4-heptanolactone