3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol

Base Information

• Chemical Name: 3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol
• CAS No.: 860438-03-5
• Molecular Formula: C₃₁H₅₀O₇
• Molecular Weight: 534.734
• Mol file: 860438-03-5.mol

Synonyms:3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol

Chemical Property of 3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol

There total 14 articles about 3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol 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: 86.0%

(4S,6S)-4-((1R,2S)-1-Benzyloxymethoxy-3-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methyl-propyl)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxane (860437-79-2) → 3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol (860438-03-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 4h;

DOI:10.1021/ol0511833

Reference yield:

1-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-5-methyl-oct-7-en-4-ol → 3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol (860438-03-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 98 percent / DIPEA; tetrabutylammonium iodide / CH₂Cl₂ / 96 h

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 96 percent / PPh₃ / CH₂Cl₂ / 5 h / 20 °C

3.1: 91 percent / KHMDS / tetrahydrofuran; toluene / 4 h / -78 °C

4.1: 95 percent / CSA / CH₂Cl₂; methanol / 3 h / 0 °C

5.1: 76 percent / AD-mix-α; (DHQ)2PHAL; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O

6.1: 85 percent / PPTS / 20 °C

7.1: 91 percent / Dess-Martin reagent; pyridine / CH₂Cl₂ / 6 h / 20 °C

8.1: Mg / tetrahydrofuran / 45 h / Heating

8.2: 90 percent / tetrahydrofuran / 2.5 h / -78 - -40 °C

9.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂; pyridine / 2 h / 20 °C

10.1: 95 percent / TBAF / H₂O; acetic acid / 48 h / 50 °C

11.1: 94 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / -78 - 20 °C

12.1: 96 percent / PPTS

13.1: 86 percent / DDQ / CH₂Cl₂; H₂O / 4 h / 0 °C

With pyridine; sodium tetrahydroborate; AD-mix-α; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; camphor-10-sulfonic acid; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; Dess-Martin periodane; ozone; magnesium; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; toluene; tert-butyl alcohol; 8.2: Grignard reaction;

DOI:10.1021/ol0511833

Reference yield:

C39H58O4Si2 (860437-99-6) → 3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol (860438-03-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 96 percent / PPh₃ / CH₂Cl₂ / 5 h / 20 °C

2.1: 91 percent / KHMDS / tetrahydrofuran; toluene / 4 h / -78 °C

3.1: 95 percent / CSA / CH₂Cl₂; methanol / 3 h / 0 °C

4.1: 76 percent / AD-mix-α; (DHQ)2PHAL; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O

5.1: 85 percent / PPTS / 20 °C

6.1: 91 percent / Dess-Martin reagent; pyridine / CH₂Cl₂ / 6 h / 20 °C

7.1: Mg / tetrahydrofuran / 45 h / Heating

7.2: 90 percent / tetrahydrofuran / 2.5 h / -78 - -40 °C

8.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂; pyridine / 2 h / 20 °C

9.1: 95 percent / TBAF / H₂O; acetic acid / 48 h / 50 °C

10.1: 94 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / -78 - 20 °C

11.1: 96 percent / PPTS

12.1: 86 percent / DDQ / CH₂Cl₂; H₂O / 4 h / 0 °C

With pyridine; sodium tetrahydroborate; AD-mix-α; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; camphor-10-sulfonic acid; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; ozone; magnesium; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; toluene; tert-butyl alcohol; 7.2: Grignard reaction;

DOI:10.1021/ol0511833

upstream raw materials:

(4S,6S)-4-((1R,2S)-1-Benzyloxymethoxy-3-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methyl-propyl)-2,2-dimethyl-6-(3-methyl-but-3-enyl)-[1,3]dioxane

4-benzyloxymethoxy-7-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-heptanal

C₃₉H₅₈O₄Si₂

(7S,8R,9S)-8-Benzyloxymethoxy-7-hydroxy-10-{(4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2,9-dimethyl-dec-1-en-5-one

Downstream raw materials:

4-((4S,6S)-6-((1R)-1-((benzyloxy)methoxy)-3-((4S,5S)-5-(3-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropyl)-2,2-dimethyl-1,3-dioxan-4-yl)butan-2-one

4-[6-(1-benzyloxymethoxy-3-{5-[11-(tert-butyl-dimethyl-silanyloxy)-6,10-bis-(tert-butyl-diphenyl-silanyloxy)-undec-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methyl-propyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-butan-2-one

3-((4S,5S)-5-{(2S,3R)-3-Benzyloxymethoxy-3-[(4S,6S)-2,2-dimethyl-6-(3-oxo-butyl)-[1,3]dioxan-4-yl]-2-methyl-propyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde