(4S,5S)-4-[(S)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolane

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Chemical Name:(4S,5S)-4-[(S)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolane
CAS No.:914083-40-2
Molecular Formula:C₂₅H₃₉N₃O₅
Molecular Weight:461.602
Hs Code.:

Synonyms:(4S,5S)-4-[(S)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolane

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Chemical Property of (4S,5S)-4-[(S)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolane

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Technology Process of (4S,5S)-4-[(S)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolane

There total 18 articles about (4S,5S)-4-[(S)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolane 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: 82.0%

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

: 914083-40-2
(4S,5S)-4-[(S)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 65 ℃; for 4h;
DOI:10.1016/j.tetlet.2006.07.107

Reference yield:

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

: 914083-40-2
(4S,5S)-4-[(S)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 10 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

8: pyridine / CH₂Cl₂ / -10 °C

9: Bu₄NBr / CH₂Cl₂ / 20 °C

10: 82 percent / NaN₃ / dimethylformamide / 4 h / 65 °C

With pyridine; AD-mix-α; lithium aluminium tetrahydride; sodium azide; methanesulfonamide; AD-mix-β; camphor-10-sulfonic acid; tetrabutylammomium bromide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 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

: 914083-40-2
(4S,5S)-4-[(S)-Azido-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-((S)-6-benzyloxy-1-methyl-hexyl)-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 11 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

9: pyridine / CH₂Cl₂ / -10 °C

10: Bu₄NBr / CH₂Cl₂ / 20 °C

11: 82 percent / NaN₃ / dimethylformamide / 4 h / 65 °C

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