(S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

Base Information

Chemical Name:(S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol
CAS No.:914083-36-6
Molecular Formula:C₂₅H₄₀O₆
Molecular Weight:436.589
Hs Code.:

Synonyms:(S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

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Chemical Property of (S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

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Technology Process of (S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

There total 15 articles about (S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 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: 85.0%

: 914083-34-4
(1S,2R)-1-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propane-1,2,3-triol

: 77-76-9
2,2-dimethoxy-propane

: 914083-36-6
(S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃;
DOI:10.1016/j.tetlet.2006.07.107

Reference yield:

: 914083-14-0
(S)-8-Benzyloxy-3-methyl-octanal

: 914083-36-6
(S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

Guidance literature:: Multi-step reaction with 7 steps

1: 86 percent / LiHMDS / tetrahydrofuran / 2 h / -78 °C

2: 90 percent / Ph₃P / benzene / 20 °C

3: AD mix-αMeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

4: CSA / CH₂Cl₂ / 1 h

5: 87 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 0 °C

6: 80 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

7: 85 percent / CSA / CH₂Cl₂ / 20 °C

With AD-mix-α; lithium aluminium tetrahydride; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; benzene; 3: Sharpless asymmetric dihydroxylation / 5: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2006.07.107

Reference yield:

: 914083-07-1
(S)-8-Benzyloxy-3-methyl-octan-1-ol

: 914083-36-6
(S)-[(4S,5S)-5-((S)-6-Benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / IBX / dimethylsulfoxide; tetrahydrofuran / 3 h / 20 °C

2: 86 percent / LiHMDS / tetrahydrofuran / 2 h / -78 °C

3: 90 percent / Ph₃P / benzene / 20 °C

4: AD mix-αMeSO2NH2 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

5: CSA / CH₂Cl₂ / 1 h

6: 87 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 0 °C

7: 80 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 - 20 °C

8: 85 percent / CSA / CH₂Cl₂ / 20 °C

With AD-mix-α; lithium aluminium tetrahydride; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; triphenylphosphine; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; benzene; 4: Sharpless asymmetric dihydroxylation / 6: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2006.07.107