N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide

Base Information

Chemical Name:N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide
CAS No.:677334-88-2
Molecular Formula:C₁₅H₁₉NO₅
Molecular Weight:293.32
Hs Code.:

Synonyms:N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide

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Chemical Property of N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide

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Technology Process of N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide

There total 10 articles about N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide 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: 78.0%

: 677334-93-9
N-((3R,3aR,6R,6aS)-2-Benzyloxy-6-methoxymethoxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide

: 677334-88-2
N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide

Guidance literature:: With hydrogenchloride; In methanol;
DOI:10.1016/j.tetlet.2003.12.135

Reference yield:

: 157831-25-9
(2R,3R,4R,5S)-1,3,4-Tris-benzyloxy-5-(4-methoxy-benzylamino)-hept-6-en-2-ol

: 677334-88-2
N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: CH₂Cl₂

1.2: 50 percent / K₂CO₃ / methanol

2.1: 49 percent / CAN / methanol

3.1: 99 percent / OsO₄; NMO / acetone; H₂O

4.1: 90 percent / p-TsOH / acetone

5.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂

6.1: 97 percent / H₂ / Pd/C / methanol

7.1: 79 percent / Bu₂SnO; Et₃N / CH₂Cl₂

8.1: 96 percent / K₂CO₃ / methanol

9.1: 82 percent / cc. HCl / methanol

10.1: 92 percent / NaIO₄ / diethyl ether; H₂O

11.1: 77 percent / Ag₂O / ethyl acetate

12.1: 78 percent / cc. HCl / methanol

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; hydrogen; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1016/j.tetlet.2003.12.135

Reference yield:

: 677334-89-3
N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-pentyl]-acetamide

: 677334-88-2
N-((3R,3aR,6R,6aR)-2-Benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / (i-Pr)2NEt / CH₂Cl₂

2: 97 percent / H₂ / Pd/C / methanol

3: 79 percent / Bu₂SnO; Et₃N / CH₂Cl₂

4: 96 percent / K₂CO₃ / methanol

5: 82 percent / cc. HCl / methanol

6: 92 percent / NaIO₄ / diethyl ether; H₂O

7: 77 percent / Ag₂O / ethyl acetate

8: 78 percent / cc. HCl / methanol

With hydrogenchloride; sodium periodate; hydrogen; di(n-butyl)tin oxide; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1016/j.tetlet.2003.12.135