(1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol

Base Information

• Chemical Name: (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol
• CAS No.: 80971-02-4
• Molecular Formula: C₂₈H₃₂O₆
• Molecular Weight: 464.558
• Mol file: 80971-02-4.mol

Synonyms:

Chemical Property of (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol

There total 23 articles about (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-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: 93.0%

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) → 1L-1,3,4-Tri-O-benzyl-2-O-methyl-chiro-inosit (80971-02-4,111466-04-7,114297-79-9)

Guidance literature:

In tetrahydrofuran; water; acetic acid; at 100 ℃;

Reference yield:

benzyl bromide (100-39-0) → (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol (80971-02-4,111466-04-7,114297-79-9)

Guidance literature:

Multi-step reaction with 10 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

10: 1 M HCl / methanol / 30 h / Heating

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) → (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol (80971-02-4,111466-04-7,114297-79-9)

Guidance literature:

Multi-step reaction with 10 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

10: 1 M HCl / methanol / 30 h / Heating

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:

1D-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-3-O-methyl-myo-inositol

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

(-)-ω-camphanate of 1D-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol

(+/-)-1,2,4-tri-O-benzyl-5,6-O-isopropylidene-myo-inositol

Downstream raw materials:

(1R)-1-L-O-methyl-myo-inositol

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

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

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