(1S,2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol

Base Information

Chemical Name:(1S,2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol
CAS No.:906748-03-6
Molecular Formula:C₄₂H₄₄O₆
Molecular Weight:644.808
Hs Code.:

Synonyms:(1S,2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol

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Chemical Property of (1S,2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol

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Technology Process of (1S,2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol

There total 17 articles about (1S,2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol 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: 100.0%

: 906641-22-3
1-methoxy-4[[(1S,2R,3R,4R,5R,6R)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]-1-cyclohexyl]oxymethyl]benzene

: 906748-03-6
(1S,2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 3h;
DOI:10.3390/10080901

Reference yield:

: 906641-09-6
(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-iodomethyl-2-methoxy-tetrahydro-pyran-3-ol

: 906748-03-6
(1S,2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol

Guidance literature:: Multi-step reaction with 15 steps

1.1: 99 percent / Et₃N; DMAP / 21 h / 20 °C

2.1: 99 percent / AgF; pyridine / 20 h / 20 °C

3.1: 86 percent / PdCl₂ / dioxane; H₂O / 3 h / 60 °C

4.1: 95 percent / MsCl; Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

5.1: CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

6.1: 95 percent / TfOH / diethyl ether / 0.17 h / 20 °C

7.1: 82 percent / aq. NaOH / methanol / 12 h / 20 °C

8.1: 95 percent / lutidine / CH₂Cl₂ / 0.17 h / 20 °C

9.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 °C

10.1: 86 percent / m-CPBA; Na₂HPO₄ / CH₂Cl₂ / 14 h / 20 °C

11.1: 66 percent / NaH / dimethylformamide; tetrahydrofuran / 2.5 h / 0 °C

12.1: tetrahydrofuran / 1 h / 20 °C

12.2: 76 percent / aq. NaOH; H₂O₂ / 0.5 h / 20 °C

13.1: TBAF / tetrahydrofuran / 48 h / 20 °C

14.1: NaH / dimethylformamide; tetrahydrofuran / 4 h / 60 °C

15.1: 100 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; cerium(III) chloride; trifluorormethanesulfonic acid; lutidine; tetrabutyl ammonium fluoride; silver fluoride; sodium hydride; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 3.1: Ferrier-II rearrangement;
DOI:10.3390/10080901

Reference yield:

: 906641-14-3
(1R,4S,5R,6R)-5,6-bis(benzyloxy)-4-hydroxycyclohex-2-en-1-yl benzoate

: 906748-03-6
(1S,2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexanol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 95 percent / TfOH / diethyl ether / 0.17 h / 20 °C

2.1: 82 percent / aq. NaOH / methanol / 12 h / 20 °C

3.1: 95 percent / lutidine / CH₂Cl₂ / 0.17 h / 20 °C

4.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 °C

5.1: 86 percent / m-CPBA; Na₂HPO₄ / CH₂Cl₂ / 14 h / 20 °C

6.1: 66 percent / NaH / dimethylformamide; tetrahydrofuran / 2.5 h / 0 °C

7.1: tetrahydrofuran / 1 h / 20 °C

7.2: 76 percent / aq. NaOH; H₂O₂ / 0.5 h / 20 °C

8.1: TBAF / tetrahydrofuran / 48 h / 20 °C

9.1: NaH / dimethylformamide; tetrahydrofuran / 4 h / 60 °C

10.1: 100 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

With sodium hydroxide; disodium hydrogenphosphate; trifluorormethanesulfonic acid; lutidine; tetrabutyl ammonium fluoride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.3390/10080901