(3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole

Base Information

• Chemical Name: (3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole
• CAS No.: 80971-00-2
• Molecular Formula: C₃₁H₃₆O₆
• Molecular Weight: 504.623
• Mol file: 80971-00-2.mol

Synonyms:

Chemical Property of (3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole

There total 20 articles about (3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[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: 87.0%

benzyl bromide (100-39-0) + 1L-5,6-O-Isopropyliden-2-O-methyl-chiro-inosit (17230-37-4) → 1L-1,3,4-Tri-O-benzyl-5,6-O-isopropyliden-2-O-methyl-chiro-inosit (80971-00-2,111466-03-6,114297-80-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 20h; Ambient temperature;

Reference yield:

benzyl bromide (100-39-0) → (3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole (80971-00-2,111466-03-6,114297-80-2)

Guidance literature:

Multi-step reaction with 9 steps

1: NaH / dimethylformamide / 2 h / 20 °C

2: 55 percent / toluene-p-sulphonic acid monohydrate / acetone; H₂O / 0.75 h / 20 °C

3: NaH / dimethylformamide / 20 °C

4: 73 percent / 1 M HCl / methanol / 0.5 h / Heating

5: 1.) dibutyltin oxide / 1.) benzene, reflux, 2 h.; 2.) DMF, 50 degC, 48 h.

6: NaH / dimethylformamide

7: 87 percent / toluene-p-sulphonic acid monohydrate / Pd/C / ethanol; H₂O / 4 h / Heating

8: 82 percent / toluene-p-sulphonic acid monohydrate / acetone / 2 h / 20 °C

9: NaH / dimethylformamide

With hydrogenchloride; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; water; N,N-dimethyl-formamide; acetone;

Reference yield:

(+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol (51548-88-0,96039-15-5,98974-89-1,128110-25-8) → (3aR,4S,5S,6R,7S,7aR)-4,5,7-Tris-benzyloxy-6-methoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole (80971-00-2,111466-03-6,114297-80-2)

Guidance literature:

Multi-step reaction with 9 steps

1: NaH / dimethylformamide / 2 h / 20 °C

2: 55 percent / toluene-p-sulphonic acid monohydrate / acetone; H₂O / 0.75 h / 20 °C

3: NaH / dimethylformamide / 20 °C

4: 73 percent / 1 M HCl / methanol / 0.5 h / Heating

5: 1.) dibutyltin oxide / 1.) benzene, reflux, 2 h.; 2.) DMF, 50 degC, 48 h.

6: NaH / dimethylformamide

7: 87 percent / toluene-p-sulphonic acid monohydrate / Pd/C / ethanol; H₂O / 4 h / Heating

8: 82 percent / toluene-p-sulphonic acid monohydrate / acetone / 2 h / 20 °C

9: NaH / dimethylformamide

With hydrogenchloride; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; water; N,N-dimethyl-formamide; acetone;

upstream raw materials:

benzyl bromide

1L-5,6-O-Isopropyliden-2-O-methyl-chiro-inosit

quebrachitol

1D-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol

Downstream raw materials:

1L-1,3,4-Tri-O-benzyl-2-O-methyl-chiro-inosit

1L-1,3,4-Tri-O-benzyl-5,6-di-O-methylsulfonyl-2-O-methyl-chiro-inosit

1L-2,3,4-Tri-O-benzyl-2-O-methyl-5-O-p-tolylsulfonyl-chiro-inosit

1L-1,3,4-Tri-O-benzyl-2-O-methyl-5-O-p-chlorphenylsulfonyl-chiro-inosit