(3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol

Base Information

• Chemical Name: (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol
• CAS No.: 266682-75-1
• Molecular Formula: C₂₃H₂₆O₄
• Molecular Weight: 366.457
• Mol file: 266682-75-1.mol

Synonyms:(3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol

Chemical Property of (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol

There total 6 articles about (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol 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: 96.0%

benzyl bromide (100-39-0) + (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol (371155-65-6) → (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol (266682-75-1)

Guidance literature:

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

DOI:10.1016/S0960-894X(03)00629-2

Reference yield: 35.0%

(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol-S,S-dioxide (266682-74-0) → (3aR,4R,8R,8aR)-2,2-Dimethyl-6,6-dioxo-hexahydro-6λ6-thiepino[4,5-d][1,3]dioxole-4,8-diol + (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol (266682-75-1)

Guidance literature:

With potassium hydroxide; In tetrachloromethane; water; tert-butyl alcohol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00011-9

Reference yield:

(3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol diacetate (371155-62-3) → (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol (266682-75-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol

2: 96 percent / NaH / dimethylformamide / 0 - 20 °C

With sodium methylate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo016237a

upstream raw materials:

(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol-S,S-dioxide

benzyl bromide

(3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol

(3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol diacetate

Downstream raw materials:

D-4,5-O-(1-methylethylidene)-3,6-bis-O-(phenylmethyl)-myo-inositol

D-2-O-benzoyl-6-O-benzyl-myo-inositol

D-2-O-benzoyl-6-O-benzyl-1,3,4,5-tetra-O-methoxymethyl-myo-inositol

D-1,3,4,5-tetra-O-methoxymethyl-myo-inositol