(1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Base Information

Chemical Name:(1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol
CAS No.:209050-74-8
Molecular Formula:C₄₅H₅₀O₁₀
Molecular Weight:750.886
Hs Code.:

Synonyms:

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Chemical Property of (1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Chemical Property:

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Technology Process of (1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

There total 15 articles about (1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol 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:

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

: 209050-74-8
(1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; water; for 16h; Yield given; Ambient temperature;
DOI:10.1016/S0040-4039(98)00737-0

Reference yield:

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

: 209050-74-8
(1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Guidance literature:: Multi-step reaction with 12 steps

1: 36 percent / dibutyltin oxide, Bu₄NBr / toluene / 4 h / Heating

2: NaH / dimethylformamide / 10 h / Ambient temperature

3: p-TsOH / methanol / 4 h / Ambient temperature

4: Et₃N, DMAP / dimethylformamide / 4 h / Ambient temperature

5: dimethylformamide / 16 h / Ambient temperature

6: p-TsOH / methanol / 14 h / Ambient temperature

7: 1.) (COCl)2, DMSO; 2.) Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

8: K₂CO₃ / acetonitrile / 20 h / Ambient temperature

9: mercuric acetate, aq. NaCl / acetone / 20 h / Ambient temperature

10: sodium triacetoxy borohydride / acetic acid; acetonitrile / 1 h / Ambient temperature

11: H⁽¹⁺⁾Sponge, Bu₄NI / acetonitrile / 48 h / 40 °C

12: NaOH / tetrahydrofuran; H₂O / 16 h / Ambient temperature

With dmap; sodium hydroxide; oxalyl dichloride; mercury(II) diacetate; tetrabutylammomium bromide; hydrogen cation; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4039(98)00737-0

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 209050-74-8
(1S,2S,3R,4S,5S,6S)-4-Benzyloxy-2,6-bis-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Guidance literature:: Multi-step reaction with 2 steps

1: H⁽¹⁺⁾Sponge, Bu₄NI / acetonitrile / 48 h / 40 °C

2: NaOH / tetrahydrofuran; H₂O / 16 h / Ambient temperature

With sodium hydroxide; hydrogen cation; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; water; acetonitrile;
DOI:10.1016/S0040-4039(98)00737-0