(2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran

Base Information

Chemical Name:(2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran
CAS No.:828914-51-8
Molecular Formula:C₁₆H₂₁N₃O₅
Molecular Weight:335.36
Hs Code.:

Synonyms:(2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran

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Chemical Property of (2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran

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Technology Process of (2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran

There total 11 articles about (2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran 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: 83.8%

: 828914-50-7
(2R,3R,3aR,6S,7R,7aR)-3-benzyloxy-2-methoxy-hexahydro-furo[3,2-b]pyran-6-ol

: 74-88-4
methyl iodide

: 828914-51-8
(2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran

Guidance literature:: (2R,3R,3aR,6S,7R,7aR)-3-benzyloxy-2-methoxy-hexahydro-furo[3,2-b]pyran-6-ol; With sodium hydride; In DMF (N,N-dimethyl-formamide); at 0 ℃; for 0.5h;

methyl iodide; In DMF (N,N-dimethyl-formamide); for 3h;

Reference yield:

: (3R,4S,5R)-2-Methoxy-5-vinyl-tetrahydro-furan-3,4-diol

: 828914-51-8
(2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran

Guidance literature:: Multi-step reaction with 9 steps

1: 58 percent / dibutyltin oxide; n-Bu₄NI; molecular sieves 4 Angstroem / acetonitrile / 5 h / Heating

2: 91 percent / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

3: 68 percent / Cl₂Ru(=CHPh)(PCy₃)2 / CH₂Cl₂ / 8 h / Heating

4: N-bromosuccinimide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

5: sodium hydroxide / tetrahydrofuran / 1 h / Heating

6: 300 mg / sodium azide / 2-methoxy-ethanol / 2 h / 126 °C

7: Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

8: NaBH₄ / methanol / 1 h / 0 °C

9: 253 mg / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; Grubbs catalyst first generation; sodium azide; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo050727b

Reference yield:

: 828914-43-8
methyl 3-O-allyl-5,6-dideoxy-β-D-ribo-hex-5-enofuranoside

: 828914-51-8
(2R,3R,3aR,6S,7R,7aR)-7-azido-3-benzyloxy-2,6-dimethoxy-hexahydrofuro[3,2-b]pyran

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

2: 68 percent / Cl₂Ru(=CHPh)(PCy₃)2 / CH₂Cl₂ / 8 h / Heating

3: N-bromosuccinimide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

4: sodium hydroxide / tetrahydrofuran / 1 h / Heating

5: 300 mg / sodium azide / 2-methoxy-ethanol / 2 h / 126 °C

6: Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

7: NaBH₄ / methanol / 1 h / 0 °C

8: 253 mg / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; Grubbs catalyst first generation; sodium azide; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo050727b