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

Base Information

Chemical Name:(7S)-3,6-anhydro-7-O-benzyl-2-deoxy-7-C-phenyl-D-altro-1,4-heptanolactone
CAS No.:250599-04-3
Molecular Formula:C₂₀H₂₀O₅
Molecular Weight:340.376
Hs Code.:

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

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

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

There total 10 articles about (7S)-3,6-anhydro-7-O-benzyl-2-deoxy-7-C-phenyl-D-altro-1,4-heptanolactone 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: 77.0%

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

: 250599-04-3
(7S)-3,6-anhydro-7-O-benzyl-2-deoxy-7-C-phenyl-D-altro-1,4-heptanolactone

Guidance literature:: With dipyridinium dichromate; In dichloromethane; for 1.5h; Heating;
DOI:10.1016/S0968-0896(99)00164-9

Reference yield:

: 100-39-0
benzyl bromide

: 250599-04-3
(7S)-3,6-anhydro-7-O-benzyl-2-deoxy-7-C-phenyl-D-altro-1,4-heptanolactone

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / NaH / dimethylformamide / 0.5 h / 20 °C

2: 86 percent / 60 percent aq. AcOH / 8 h / 20 °C

3: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

4: 85 percent / NaI / butan-2-one / 12 h / Heating

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

6: 85 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O / 3 h / 20 °C

7: 77 percent / PDC / CH₂Cl₂ / 1.5 h / Heating

With dipyridinium dichromate; sulfuric acid; oxygen; sodium hydride; acetic acid; triethylamine; sodium iodide; copper(l) chloride; palladium dichloride; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; butanone; 1: Alkylation / 2: Ring cleavage / 3: mesylation / 4: Elimination / 5: Ring cleavage / 6: Cyclization / 7: Oxidation;
DOI:10.1016/S0968-0896(99)00164-9

Reference yield:

: 201863-41-4
(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

: 250599-04-3
(7S)-3,6-anhydro-7-O-benzyl-2-deoxy-7-C-phenyl-D-altro-1,4-heptanolactone

Guidance literature:: Multi-step reaction with 9 steps

1: 83 percent / PPh₃; DEAD / tetrahydrofuran / 8 h / 0 - 20 °C

2: 93 percent / NaOMe / methanol / 1.5 h / 20 °C

3: 96 percent / NaH / dimethylformamide / 0.5 h / 20 °C

4: 86 percent / 60 percent aq. AcOH / 8 h / 20 °C

5: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

6: 85 percent / NaI / butan-2-one / 12 h / Heating

7: 86 percent / 5 percent aq. H₂SO₄ / dioxane / 1 h / Heating

8: 85 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O / 3 h / 20 °C

9: 77 percent / PDC / CH₂Cl₂ / 1.5 h / Heating

With dipyridinium dichromate; sulfuric acid; oxygen; sodium methylate; sodium hydride; acetic acid; triethylamine; triphenylphosphine; sodium iodide; copper(l) chloride; palladium dichloride; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; butanone; 1: Acylation / 2: Hydrolysis / 3: Alkylation / 4: Ring cleavage / 5: mesylation / 6: Elimination / 7: Ring cleavage / 8: Cyclization / 9: Oxidation;
DOI:10.1016/S0968-0896(99)00164-9