(2R,3R,4S,5S,6R,7S,8S)-5,7,9-Tris-benzyloxy-2,4,6,8-tetramethyl-nonane-1,3-diol

Base Information

Chemical Name:(2R,3R,4S,5S,6R,7S,8S)-5,7,9-Tris-benzyloxy-2,4,6,8-tetramethyl-nonane-1,3-diol
CAS No.:123363-75-7
Molecular Formula:C₃₄H₄₆O₅
Molecular Weight:534.736
Hs Code.:

Synonyms:

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Chemical Property of (2R,3R,4S,5S,6R,7S,8S)-5,7,9-Tris-benzyloxy-2,4,6,8-tetramethyl-nonane-1,3-diol

Chemical Property:

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Useful:

Technology Process of (2R,3R,4S,5S,6R,7S,8S)-5,7,9-Tris-benzyloxy-2,4,6,8-tetramethyl-nonane-1,3-diol

There total 16 articles about (2R,3R,4S,5S,6R,7S,8S)-5,7,9-Tris-benzyloxy-2,4,6,8-tetramethyl-nonane-1,3-diol 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:

: (Z)-(3R,4R)-3-Hydroxy-4-methyl-hept-5-enal

: 123363-75-7
(2R,3R,4S,5S,6R,7S,8S)-5,7,9-Tris-benzyloxy-2,4,6,8-tetramethyl-nonane-1,3-diol

Guidance literature:: Multi-step reaction with 15 steps

1: NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / from -5 deg C to RT

2: diethyl ether / Ambient temperature

3: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -50 - -20 °C

4: LAH / tetrahydrofuran / 0 °C

5: 60 percent / VO(acac)2, TBHP / CH₂Cl₂ / from -20 deg C to RT

6: NaH / tetrahydrofuran; dimethylformamide / 50 °C

7: BF₃*OEt₂ / tetrahydrofuran / from -78 deg C to -20 deg C

8: H₂, quinoline / Pd-CaCO₃ / benzene / Ambient temperature

9: 2,6-dimethylpyridine / CH₂Cl₂ / Ambient temperature

10: 67 percent / WO₅*HMPA / CH₂Cl₂ / Ambient temperature

11: n-Bu₄NF / tetrahydrofuran / Ambient temperature

12: NaH / tetrahydrofuran; dimethylformamide / 50 °C

13: tetrahydrofuran / 0 °C

14: MeI, CaCO₃ / dimethylformamide; H₂O

15: LAH / tetrahydrofuran / from -78 deg C to -20 deg C

With 2,6-dimethylpyridine; quinoline; tert.-butylhydroperoxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; bis(acetylacetonate)oxovanadium; WO₅*HMPA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; calcium carbonate; lithium diisopropyl amide; methyl iodide; Lindlar's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1246/cl.1989.117

Reference yield:

: 123363-70-2,123410-28-6
(2R,3R,4S)-2-Methyl-4-((2S,3R)-3-methyl-oxiranyl)-pentane-1,3-diol

: 123363-75-7
(2R,3R,4S,5S,6R,7S,8S)-5,7,9-Tris-benzyloxy-2,4,6,8-tetramethyl-nonane-1,3-diol

Guidance literature:: Multi-step reaction with 10 steps

1: NaH / tetrahydrofuran; dimethylformamide / 50 °C

2: BF₃*OEt₂ / tetrahydrofuran / from -78 deg C to -20 deg C

3: H₂, quinoline / Pd-CaCO₃ / benzene / Ambient temperature

4: 2,6-dimethylpyridine / CH₂Cl₂ / Ambient temperature

5: 67 percent / WO₅*HMPA / CH₂Cl₂ / Ambient temperature

6: n-Bu₄NF / tetrahydrofuran / Ambient temperature

7: NaH / tetrahydrofuran; dimethylformamide / 50 °C

8: tetrahydrofuran / 0 °C

9: MeI, CaCO₃ / dimethylformamide; H₂O

10: LAH / tetrahydrofuran / from -78 deg C to -20 deg C

With 2,6-dimethylpyridine; quinoline; lithium aluminium tetrahydride; WO₅*HMPA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; calcium carbonate; methyl iodide; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1246/cl.1989.117

Reference yield:

: 123363-69-9
(Z)-(2R,3S,4R)-2,4-Dimethyl-hept-5-ene-1,3-diol

: 123363-75-7
(2R,3R,4S,5S,6R,7S,8S)-5,7,9-Tris-benzyloxy-2,4,6,8-tetramethyl-nonane-1,3-diol

Guidance literature:: Multi-step reaction with 11 steps

1: 60 percent / VO(acac)2, TBHP / CH₂Cl₂ / from -20 deg C to RT

2: NaH / tetrahydrofuran; dimethylformamide / 50 °C

3: BF₃*OEt₂ / tetrahydrofuran / from -78 deg C to -20 deg C

4: H₂, quinoline / Pd-CaCO₃ / benzene / Ambient temperature

5: 2,6-dimethylpyridine / CH₂Cl₂ / Ambient temperature

6: 67 percent / WO₅*HMPA / CH₂Cl₂ / Ambient temperature

7: n-Bu₄NF / tetrahydrofuran / Ambient temperature

8: NaH / tetrahydrofuran; dimethylformamide / 50 °C

9: tetrahydrofuran / 0 °C

10: MeI, CaCO₃ / dimethylformamide; H₂O

11: LAH / tetrahydrofuran / from -78 deg C to -20 deg C

With 2,6-dimethylpyridine; quinoline; tert.-butylhydroperoxide; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; WO₅*HMPA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; calcium carbonate; methyl iodide; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1246/cl.1989.117