(3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-nitro-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-nitro-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS No.: 866850-55-7
• Molecular Formula: C₂₇H₃₇NO₁₀
• Molecular Weight: 535.591
• Mol file: 866850-55-7.mol

Synonyms:(3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-nitro-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-nitro-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl]-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,5R,6R,6aR)-6-Allyl-6-benzyloxy-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-nitro-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 5 articles about (3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-nitro-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl]-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: 65.0%

(3aR,5S,6S,6aR)-6-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (866850-49-9) + nitromethane (75-52-5) → (3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-nitro-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (866850-55-7)

Guidance literature:

(3aR,5S,6S,6aR)-6-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde; nitromethane; With potassium fluoride; In isopropyl alcohol; at 25 ℃; for 24h;

With dmap; acetic anhydride; In diethyl ether; at 25 ℃; for 12h;

With sodium tetrahydroborate; In ethanol; at 25 ℃; for 6h;

DOI:10.1021/jo050689w

Reference yield:

Methanesulfonic acid (3aR,5R,6R,6aR)-6-allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (866850-43-3) → (3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-nitro-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (866850-55-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrabutylammonium bromide; NaOH / H₂O / 70 h / 70 °C

2.1: acetic acid / H₂O / 15 h / 25 °C

3.1: 98 percent / NaIO₄ / methanol; H₂O / 2 h / 25 °C

4.1: KF / propan-2-ol / 24 h / 25 °C

4.2: acetic anhydride; 4-(dimethylamino)pyridine / diethyl ether / 12 h / 25 °C

4.3: 65 percent / NaBH₄ / ethanol / 6 h / 25 °C

With potassium fluoride; sodium hydroxide; sodium periodate; tetrabutylammomium bromide; acetic acid; In methanol; water; isopropyl alcohol;

DOI:10.1021/jo050689w

Reference yield:

(R)-1-[(3aR,5R,6S,6aR)-6-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol (866850-47-7) → (3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-5-[(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-nitro-ethyl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (866850-55-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / NaIO₄ / methanol; H₂O / 2 h / 25 °C

2.1: KF / propan-2-ol / 24 h / 25 °C

2.2: acetic anhydride; 4-(dimethylamino)pyridine / diethyl ether / 12 h / 25 °C

2.3: 65 percent / NaBH₄ / ethanol / 6 h / 25 °C

With potassium fluoride; sodium periodate; In methanol; water; isopropyl alcohol;

DOI:10.1021/jo050689w

upstream raw materials:

(3aR,5S,6S,6aR)-6-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

nitromethane

Methanesulfonic acid (3aR,5R,6R,6aR)-6-allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

(R)-1-[(3aR,5R,6S,6aR)-6-((3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol