(1R,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexanecarbaldehyde

Base Information

Chemical Name:(1R,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexanecarbaldehyde
CAS No.:921771-20-2
Molecular Formula:C₃₅H₃₆O₅
Molecular Weight:536.668
Hs Code.:

Synonyms:(1R,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexanecarbaldehyde

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Chemical Property of (1R,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexanecarbaldehyde

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Technology Process of (1R,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexanecarbaldehyde

There total 11 articles about (1R,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexanecarbaldehyde 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: 81.0%

: 921771-19-9
(S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-1,2-diol

: 921771-20-2
(1R,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexanecarbaldehyde

Guidance literature:: With sodium periodate; In water; acetonitrile; at 0 ℃; for 1h;
DOI:10.1021/jo061717t

Reference yield:

: 921771-14-4
(1S,4S,5R)-5-[(2S)-1,4-dioxa-spiro[4.5]dec-2-yl]-cyclohex-2-ene-1,4-diol

: 921771-20-2
(1R,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 2 h / 20 °C

1.2: 69 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

2.1: 85 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / acetone; H₂O / 16 h / 20 °C

3.1: NaH / tetrahydrofuran / 2 h / 20 °C

3.2: 72 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

4.1: 82 percent / aq. acetic acid / 14 h / 20 °C

5.1: 81 percent / NaIO₄ / acetonitrile; H₂O / 1 h / 0 °C

With sodium periodate; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; water; acetone; acetonitrile;
DOI:10.1021/jo061717t

Reference yield:

: 921770-79-8
(5R)-5-[(2S)-1,4-dioxa-spiro[4.5]dec-2-yl]-cyclohex-3-enone

: 921771-20-2
(1R,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexanecarbaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1.1: 92 percent / LiAlH₄ / diethyl ether / 1 h / -60 °C

2.1: 92 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

3.1: 89 percent / m-CPBA / 1,2-dichloro-ethane / 8 h / 20 °C

4.1: diphenyl diselenide; sodium borohydride / ethanol / 2 h / 20 °C

4.2: 41 percent / aq. H₂O₂ / ethanol; tetrahydrofuran / 1.5 h / 70 °C

5.1: NaH / tetrahydrofuran / 2 h / 20 °C

5.2: 69 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

6.1: 85 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / acetone; H₂O / 16 h / 20 °C

7.1: NaH / tetrahydrofuran / 2 h / 20 °C

7.2: 72 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

8.1: 82 percent / aq. acetic acid / 14 h / 20 °C

9.1: 81 percent / NaIO₄ / acetonitrile; H₂O / 1 h / 0 °C

With dmap; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; diphenyl diselenide; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; acetonitrile;
DOI:10.1021/jo061717t