(2S,3a'R,5'R,6'S,6a'S)-6'-benzyloxy-5'-methyl-3a',5',6',6a'-tetrahydro-3'H,5H-spiro-[furan-2,2'-furo[3,2-b]furan]-5-one

Base Information

Chemical Name:(2S,3a'R,5'R,6'S,6a'S)-6'-benzyloxy-5'-methyl-3a',5',6',6a'-tetrahydro-3'H,5H-spiro-[furan-2,2'-furo[3,2-b]furan]-5-one
CAS No.:1346433-82-6
Molecular Formula:C₁₇H₁₈O₅
Molecular Weight:302.327
Hs Code.:

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Chemical Property of (2S,3a'R,5'R,6'S,6a'S)-6'-benzyloxy-5'-methyl-3a',5',6',6a'-tetrahydro-3'H,5H-spiro-[furan-2,2'-furo[3,2-b]furan]-5-one

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Technology Process of (2S,3a'R,5'R,6'S,6a'S)-6'-benzyloxy-5'-methyl-3a',5',6',6a'-tetrahydro-3'H,5H-spiro-[furan-2,2'-furo[3,2-b]furan]-5-one

There total 11 articles about (2S,3a'R,5'R,6'S,6a'S)-6'-benzyloxy-5'-methyl-3a',5',6',6a'-tetrahydro-3'H,5H-spiro-[furan-2,2'-furo[3,2-b]furan]-5-one 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:

: C₁₇H₂₀O₅

: 1346433-82-6
(2S,3a'R,5'R,6'S,6a'S)-6'-benzyloxy-5'-methyl-3a',5',6',6a'-tetrahydro-3'H,5H-spiro-[furan-2,2'-furo[3,2-b]furan]-5-one

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide; at 0 ℃; for 8h; Molecular sieve; Inert atmosphere;
DOI:10.1021/jo201570h

Reference yield:

: 1346433-81-5
(2R,3S,4R,5R)-4-benzyloxy-2-(furan-2-ylmethyl)-5-methyltetrahydrofuran-3-ol

: 1346433-82-6
(2S,3a'R,5'R,6'S,6a'S)-6'-benzyloxy-5'-methyl-3a',5',6',6a'-tetrahydro-3'H,5H-spiro-[furan-2,2'-furo[3,2-b]furan]-5-one

Guidance literature:: Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 °C / Inert atmosphere

2: dipyridinium dichromate / N,N-dimethyl-formamide / 8 h / 0 °C / Molecular sieve; Inert atmosphere

With dipyridinium dichromate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo201570h

Reference yield:

: (3R,4R,5R)-4-(benzyloxy)-5-methyltetrahydro-2,3-furandiol

: 1346433-82-6
(2S,3a'R,5'R,6'S,6a'S)-6'-benzyloxy-5'-methyl-3a',5',6',6a'-tetrahydro-3'H,5H-spiro-[furan-2,2'-furo[3,2-b]furan]-5-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 0 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: camphor-10-sulfonic acid / methanol / 4 h / 0 - 20 °C

5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: n-butyllithium / diethyl ether; hexane / 1 h / -15 - 20 °C / Inert atmosphere

6.2: 5 h / 0 - 20 °C / Inert atmosphere

7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

7.2: 0.5 h / 0 °C / Inert atmosphere

7.3: 0 - 20 °C / Inert atmosphere

8.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 8 h / Inert atmosphere; Reflux

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / pH 7 / aq. phosphate buffer

10.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 °C / Inert atmosphere

11.1: dipyridinium dichromate / N,N-dimethyl-formamide / 8 h / 0 °C / Molecular sieve; Inert atmosphere

With 1H-imidazole; dipyridinium dichromate; n-butyllithium; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; potassium tert-butylate; tri-n-butyl-tin hydride; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jo201570h