2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol

Base Information

• Chemical Name: 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol
• CAS No.: 158215-59-9
• Molecular Formula: C₅₂H₅₅O₁₀P
• Molecular Weight: 870.976

Synonyms:2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol

Chemical Property of 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol

There total 13 articles about 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol 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:

methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside (2595-06-4,18685-19-3,40653-13-2,40653-30-3,67583-56-6,68027-26-9,73111-52-1) → 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol (158215-59-9)

Guidance literature:

Multi-step reaction with 11 steps

1: p-TsOH / methanol; CH₂Cl₂ / 12 h / Ambient temperature

2: 74 percent / pyridine, Ph₃P, CI₄ / 12 h / Ambient temperature

3: 95percent NaH / dimethylformamide / 20 h

4: 1.) aq. HgCl₂, 2.) MsCl, DMAP, pyridine / 1.) acetone, 100 deg C, 1.5 h, 2.) r.t., 4 h

5: 1.) CeCl₃*7H₂O, 2.) NaBH₄ / 1.) MeOH, -50 deg C, 10 min, 2.) -50 deg C, 5 h

6: 55percent m-CPBA / CH₂Cl₂ / 24 h / Ambient temperature

7: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 3.5 h / Ambient temperature

8: 85 percent / Bu₂SnO, 3 Angstroem molecular sieves, Bu₄NBr / acetonitrile / 5 h / 80 °C

9: 89 percent / PCC / CH₂Cl₂ / 13 h / Ambient temperature

10: 1.) (R)-Alpine hydride, 2.) 3 M aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, -90 deg C, 30 min, 2.) O deg C, 30 min

11: 1.) tetrazole, 2.) aq. NaIO₄ / 2.) RuCl₃*3H₂O / 1.) MeCN, CH₂Cl₂, r.t., 1.5 h, 2.) 0 deg C, 0.5 h

With pyridine; 1H-tetrazole; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; R-Alpine-Hydride; carbon tetraiodide; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutylammomium bromide; dihydrogen peroxide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; mercury dichloride; ruthenium trichloride; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00090a035

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol (158215-59-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 74 percent / pyridine, Ph₃P, CI₄ / 12 h / Ambient temperature

2: 95percent NaH / dimethylformamide / 20 h

3: 1.) aq. HgCl₂, 2.) MsCl, DMAP, pyridine / 1.) acetone, 100 deg C, 1.5 h, 2.) r.t., 4 h

4: 1.) CeCl₃*7H₂O, 2.) NaBH₄ / 1.) MeOH, -50 deg C, 10 min, 2.) -50 deg C, 5 h

5: 55percent m-CPBA / CH₂Cl₂ / 24 h / Ambient temperature

6: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 3.5 h / Ambient temperature

7: 85 percent / Bu₂SnO, 3 Angstroem molecular sieves, Bu₄NBr / acetonitrile / 5 h / 80 °C

8: 89 percent / PCC / CH₂Cl₂ / 13 h / Ambient temperature

9: 1.) (R)-Alpine hydride, 2.) 3 M aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, -90 deg C, 30 min, 2.) O deg C, 30 min

10: 1.) tetrazole, 2.) aq. NaIO₄ / 2.) RuCl₃*3H₂O / 1.) MeCN, CH₂Cl₂, r.t., 1.5 h, 2.) 0 deg C, 0.5 h

With pyridine; 1H-tetrazole; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; R-Alpine-Hydride; carbon tetraiodide; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutylammomium bromide; dihydrogen peroxide; sodium hydride; di(n-butyl)tin oxide; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; mercury dichloride; ruthenium trichloride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00090a035

Reference yield:

(4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one (85798-11-4) → 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-O-(p-methoxybenzyl)-D-myo-inositol (158215-59-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) CeCl₃*7H₂O, 2.) NaBH₄ / 1.) MeOH, -50 deg C, 10 min, 2.) -50 deg C, 5 h

2: 55percent m-CPBA / CH₂Cl₂ / 24 h / Ambient temperature

3: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 3.5 h / Ambient temperature

4: 85 percent / Bu₂SnO, 3 Angstroem molecular sieves, Bu₄NBr / acetonitrile / 5 h / 80 °C

5: 89 percent / PCC / CH₂Cl₂ / 13 h / Ambient temperature

6: 1.) (R)-Alpine hydride, 2.) 3 M aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, -90 deg C, 30 min, 2.) O deg C, 30 min

7: 1.) tetrazole, 2.) aq. NaIO₄ / 2.) RuCl₃*3H₂O / 1.) MeCN, CH₂Cl₂, r.t., 1.5 h, 2.) 0 deg C, 0.5 h

With 1H-tetrazole; sodium hydroxide; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; R-Alpine-Hydride; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutylammomium bromide; dihydrogen peroxide; di(n-butyl)tin oxide; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; ruthenium trichloride; In dichloromethane; acetonitrile;

DOI:10.1021/jo00090a035

upstream raw materials:

Dibenzyl N,N-diisopropylphosphoramidite

2-O-Allyl-3,4,5-tri-O-benzyl-6-O-(p-methoxybenzyl)-myo-inositol

methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

Downstream raw materials:

2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Phosphoric acid (1R,2R,3R,4R,5S,6R)-2-allyloxy-6-((2R,3R,4R,5S,6R)-3-azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-cyclohexyl ester dibenzyl ester

3,4,5-Tri-O-benzyl-1-O-(dibenzylphosphono)-6-(2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-D-myo-inositol

6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate

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