Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester

Base Information

Chemical Name:Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester
CAS No.:214068-40-3
Molecular Formula:C₃₈H₄₂O₉
Molecular Weight:642.746
Hs Code.:

Synonyms:Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester

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Chemical Property of Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester

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Technology Process of Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester

There total 12 articles about Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl 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: 89.0%

: 214068-38-9
Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester

: 214068-40-3
Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 3h; Ambient temperature;
DOI:10.1021/jo980501r

Reference yield:

: 3162-96-7
methyl 4,6-O-benzylidene-α-D-glucopyranoside

: 214068-40-3
Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 56 percent / Bu₂SnO, Bu₄NBr / toluene / Heating

2: 83 percent / p-TsOH monohydrate / methanol / 2 h / Ambient temperature

3: 65 percent / DMAP, Et₃N / dimethylformamide / Ambient temperature; overnight

4: 95 percent / NaH / dimethylformamide / 2 h / Ambient temperature

5: 42 percent / aq. H₂SO₄ / methanol; acetone / 1 h / Ambient temperature

6: (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 078 deg C to rt

7: K₂CO₃ / acetonitrile / Heating; overnight

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

9: 83 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 0.75 h / Ambient temperature

10: 57 percent / proton sponge, n-Bu₄NBr / acetonitrile / rt to 55 deg C

11: 89 percent / DDQ / CH₂Cl₂ / 3 h / Ambient temperature

With dmap; oxalyl dichloride; Proton Sponge; sulfuric acid; mercury(II) diacetate; tetrabutylammomium bromide; sodium tris(acetoxy)borohydride; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium chloride; In methanol; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/jo980501r

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 214068-40-3
Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-hydroxy-cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 57 percent / proton sponge, n-Bu₄NBr / acetonitrile / rt to 55 deg C

2: 89 percent / DDQ / CH₂Cl₂ / 3 h / Ambient temperature

With Proton Sponge; tetrabutylammomium bromide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; acetonitrile;
DOI:10.1021/jo980501r