(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS No.: 133839-52-8
• Molecular Formula: C₂₂H₃₂O₇
• Molecular Weight: 408.492
• Mol file: 133839-52-8.mol

Synonyms:(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 1 articles about (3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 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: 97.0%

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside (18427-19-5) + p-methoxybenzyl chloride (824-94-2) → (3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (133839-52-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (133839-52-8) → (2R,4R,5S,6S,7R)-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decene-1,5,7-triol (133839-45-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 2percent H₂SO₄ / methanol / 5 h / Ambient temperature

2: imidazole / CH₂Cl₂ / 1 h / ice-bath

3: 97.9 percent / pyridine / 6 h / Ambient temperature

4: 91 percent / 1N HCl / tetrahydrofuran / 1 h / Ambient temperature

5: 96 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

6: 1) NaH / 1) DMF, r.t., 30 min, 2) 60 deg C, 90 min

7: 1) NaH / 1) THF, DMSO, r.t., 2h, 2) 12h

8: 3N H₂SO₄ / dioxane / 48 h / Ambient temperature

9: NaIO₄ / H₂O; methanol / 2 h / 5 °C

11: 1) DIBAH, 2) CSA / 1) CH₂Cl₂, hexane, -80 deg C, 1h, 2) r.t., 1h

12: 77.8 percent / H₂ / Raney-Ni W-2 / ethanol / 9 h / 760 Torr / Ambient temperature

13: 1) (COCl₂)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -90 deg C, 30 min, 2) -90 to -70 deg C, 1h

14: 1) MgBr₂*Et₂O / 1) CH₂Cl₂, Et₂O, -60 deg C, 10 min, 2) <60 deg C, 15 min

15: 80 percent / 1N HCl / tetrahydrofuran / 6 h / 50 °C

16: 91 percent / Ca(BH₄)2 / ethanol / 3 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; sodium periodate; calcium borohydride; (COCl₂)2; sulfuric acid; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; magnesium bromide; Raney-Ni W-2; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water;

DOI:10.1248/cpb.39.64

Reference yield:

(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (133839-52-8) → (2R,4R,5S,6S,7R)-5,7-isopropylidenedioxy-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decenol (129250-98-2)

Guidance literature:

Multi-step reaction with 17 steps

1: 2percent H₂SO₄ / methanol / 5 h / Ambient temperature

2: imidazole / CH₂Cl₂ / 1 h / ice-bath

3: 97.9 percent / pyridine / 6 h / Ambient temperature

4: 91 percent / 1N HCl / tetrahydrofuran / 1 h / Ambient temperature

5: 96 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

6: 1) NaH / 1) DMF, r.t., 30 min, 2) 60 deg C, 90 min

7: 1) NaH / 1) THF, DMSO, r.t., 2h, 2) 12h

8: 3N H₂SO₄ / dioxane / 48 h / Ambient temperature

9: NaIO₄ / H₂O; methanol / 2 h / 5 °C

11: 1) DIBAH, 2) CSA / 1) CH₂Cl₂, hexane, -80 deg C, 1h, 2) r.t., 1h

12: 77.8 percent / H₂ / Raney-Ni W-2 / ethanol / 9 h / 760 Torr / Ambient temperature

13: 1) (COCl₂)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -90 deg C, 30 min, 2) -90 to -70 deg C, 1h

14: 1) MgBr₂*Et₂O / 1) CH₂Cl₂, Et₂O, -60 deg C, 10 min, 2) <60 deg C, 15 min

15: 80 percent / 1N HCl / tetrahydrofuran / 6 h / 50 °C

16: 91 percent / Ca(BH₄)2 / ethanol / 3 h / Ambient temperature

17: 90 percent / CSA / benzene / 2 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; sodium periodate; calcium borohydride; (COCl₂)2; sulfuric acid; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; magnesium bromide; Raney-Ni W-2; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; benzene;

DOI:10.1248/cpb.39.64

upstream raw materials:

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside

p-methoxybenzyl chloride

Downstream raw materials:

(R)-1-{(3aR,5S,6R,6aR)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl}-ethane-1,2-diol

(2R,4R,5S,6S,7R)-6-methoxy-4-<2-(4-methoxybenzyloxy)ethyl>-2-methyl-9-decene-1,5,7-triol

(3aR,5S,6R,6aR)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-5-(S)-oxiranyl-tetrahydro-furo[2,3-d][1,3]dioxole

2(S)-<2(S)-isopropyloxy-5(R)-<2-(4-methoxybenzyloxy)ethyl>-3(R)-methyl-6(S)-tetrahydropyranyl>-2-methoxyethanol