(1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane
• CAS No.: 1040727-24-9
• Molecular Formula: C₂₇H₄₂O₅
• Molecular Weight: 446.627
• Mol file: 1040727-24-9.mol

Synonyms:(1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane

Chemical Property of (1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane

There total 12 articles about (1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane 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: 94.0%

(2S,3S,4R,5R,6R)-1-(benzyloxy)-6-((1S,3S,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]-octan-3-yl)-2,4-dimethylheptane-3,5-diol (1040727-35-2) + 2,2-dimethoxy-propane (77-76-9) → (1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane (1040727-24-9)

Guidance literature:

With pyridinium p-toluenesulfonate; at 20 ℃; optical yield given as %de;

DOI:10.1021/ol801148d

Reference yield: 83.0%

(2S,3R,4R,5S)-2-{(4S,5R,6S)-6-[(S)-1-(benzyloxy)propan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}-4-methylnon-8-ene-3,5-diol → (1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane (1040727-24-9)

Guidance literature:

With oxygen; copper dichloride; palladium dichloride; In tetrahydrofuran; at 0 ℃; for 24h;

DOI:10.1002/ejoc.201300012

Reference yield:

(2S,3R,4R)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanoic acid methoxy-methyl-amide (172269-19-1) → (1S,3R,4R,5S)-3-((R)-1-{(4R,5R,6S)-6-[(S)-1-(benzyloxy)propano-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethyl)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane (1040727-24-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1.67 h / 0 - 25 °C / Inert atmosphere

2.1: tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / acetic acid / 0.67 h / Inert atmosphere

5.1: camphor-10-sulfonic acid / 18 h / 20 - 25 °C / Inert atmosphere

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 - 20 °C / pH 7.0

7.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.5 h / -78 °C / Inert atmosphere

7.2: 1.5 h / -78 °C / Inert atmosphere

8.1: magnesium / tetrahydrofuran / 4.5 h / 20 °C / Inert atmosphere

8.2: 2 h / -78 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C

10.1: copper dichloride; palladium dichloride; oxygen / tetrahydrofuran / 24 h / 0 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; sodium tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; oxygen; titanium tetrachloride; magnesium; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper dichloride; palladium dichloride; In tetrahydrofuran; dichloromethane; acetic acid; dimethyl sulfoxide; 3.1: |Aldol Condensation / 7.1: |Swern Oxidation;

DOI:10.1002/ejoc.201300012

upstream raw materials:

(2S,3S,4R,5R,6R)-1-(benzyloxy)-6-((1S,3S,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]-octan-3-yl)-2,4-dimethylheptane-3,5-diol

2,2-dimethoxy-propane

(2S,3R,4R)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanoic acid methoxy-methyl-amide

(S)-4-benzyl-3-{(2S,3R,4R)-3-hydroxy-5-[(4methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one