<3aR(3aα,5β,6α,6aα)>-tetrahydro-2,2-dimethyl-5-acetoxy-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole

Base Information

• Chemical Name: <3aR(3aα,5β,6α,6aα)>-tetrahydro-2,2-dimethyl-5-acetoxy-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole
• CAS No.: 120520-94-7
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331
• Mol file: 120520-94-7.mol

Synonyms:<3aR(3aα,5β,6α,6aα)>-tetrahydro-2,2-dimethyl-5-acetoxy-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole

Chemical Property of <3aR(3aα,5β,6α,6aα)>-tetrahydro-2,2-dimethyl-5-acetoxy-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3aR(3aα,5β,6α,6aα)>-tetrahydro-2,2-dimethyl-5-acetoxy-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole

There total 2 articles about <3aR(3aα,5β,6α,6aα)>-tetrahydro-2,2-dimethyl-5-acetoxy-6-(phenylmethoxy)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: 83.0%

lead(IV) tetraacetate (546-67-8) + 1,2-O-(methylethylidene)-3-O-(phenylmethyl)-α-D-ribofuranuroic acid (120417-90-5) → <3aR(3aα,5β,6α,6aα)>-tetrahydro-2,2-dimethyl-5-acetoxy-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole (120520-94-7)

Guidance literature:

With pyridine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(00)82295-9

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (63593-02-2) → <3aR(3aα,5β,6α,6aα)>-tetrahydro-2,2-dimethyl-5-acetoxy-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole (120520-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / H₂O₂, NaH₂PO₄, NaClO₂ / acetonitrile; H₂O / 10 h / 15 °C

2: 83 percent / pyridine / acetonitrile / 2.5 h / 20 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In water; acetonitrile;

DOI:10.1021/jo00278a022

Reference yield: 85.0%

<3aR(3aα,5β,6α,6aα)>-tetrahydro-2,2-dimethyl-5-acetoxy-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole (120520-94-7) → (3aR,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (76768-64-4,121701-07-3,121701-08-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 3h;

DOI:10.1016/S0040-4039(00)82295-9

upstream raw materials:

lead(IV) tetraacetate

1,2-O-(methylethylidene)-3-O-(phenylmethyl)-α-D-ribofuranuroic acid

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

Downstream raw materials:

2-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-phenyl-ethanone

2-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-phenyl-ethanone

1-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propan-2-one

<3aR(3aα,5β,6β,6aα)>-tetrahydro-2,2-dimethyl-5-(2-oxopropyl)-6-(phenylmethoxy)furo<2,3-d>-1,3-dioxole