Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Base Information

Chemical Name:Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
CAS No.:1054640-00-4
Molecular Formula:C₆₃H₇₀O₁₆P₂
Molecular Weight:1145.19
Hs Code.:

Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

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Chemical Property of Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

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Technology Process of Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

There total 18 articles about Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 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:

: 3587-60-8
Benzyloxymethyl chloride

: 1054640-00-4
Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: proton sponge, n-Bu₄NBr / acetonitrile / rt to 55 deg C

2: aq. NaOH / methanol / 2 h / Heating

3: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, rt, 30 min, 2.) -40 deg C to rt, 60 min

4: 69 percent / DDQ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

5: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, rt, 30 min, 2.) -40 deg C to rt, 60 min

With 1H-tetrazole; sodium hydroxide; Proton Sponge; tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo980501r

Reference yield:

: 100-39-0
benzyl bromide

: 1054640-00-4
Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: NaH / dimethylformamide / 2 h / Ambient temperature

2: p-TsOH monohydrate / methanol / 1 h / Ambient temperature

3: (COCl)2, Et₃N / CH₂Cl₂; dimethylsulfoxide / -78 deg C to rt

4: K₂CO₃ / acetonitrile / Heating; overnight

5: 1.) Hg(OAc)2, 2.) NaCl / 1.) acetone, H₂O, 45 min, 2.) rt, 24 h

6: 81 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 0.75 h / Ambient temperature

7: proton sponge, n-Bu₄NBr / acetonitrile / rt to 55 deg C

8: aq. NaOH / methanol / 2 h / Heating

9: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, rt, 30 min, 2.) -40 deg C to rt, 60 min

10: 69 percent / DDQ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

11: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, rt, 30 min, 2.) -40 deg C to rt, 60 min

With 1H-tetrazole; sodium hydroxide; oxalyl dichloride; Proton Sponge; mercury(II) diacetate; tetrabutylammomium bromide; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium chloride; In methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo980501r

Reference yield:

: 108549-21-9
benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite

: 1054640-00-4
Phosphoric acid benzyl ester (1S,2R,3S,4S,5R,6R)-3,4-bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyl ester (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / diisopropylammonium tetrazole / CH₂Cl₂ / 1 h / Ambient temperature

2: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, rt, 30 min, 2.) -40 deg C to rt, 60 min

3: 69 percent / DDQ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

4: 1.) 1H-tetrazole, 2.) m-CPBA / 1.) CH₂Cl₂, rt, 30 min, 2.) -40 deg C to rt, 60 min

With 1H-tetrazole; N,N-diisopropylamine tetrazolide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;
DOI:10.1021/jo980501r