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

Base Information

• Chemical Name: (1S,2S,3S,4S,5R,6S)-3-Benzyloxy-2,6-bis-benzyloxymethoxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol
• CAS No.: 186541-50-4
• Molecular Formula: C₄₅H₅₀O₁₀
• Molecular Weight: 750.886
• Mol file: 186541-50-4.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (1S,2S,3S,4S,5R,6S)-3-Benzyloxy-2,6-bis-benzyloxymethoxy-4,5-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:

p-methoxybenzyl chloride (824-94-2) → (1S,2S,3S,4S,5R,6S)-3-Benzyloxy-2,6-bis-benzyloxymethoxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol (186541-50-4)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH / dimethylformamide / 50 °C

2: 25 percent / DIBAL-H

3: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.75 h / -78 - 20 °C

4: K₂CO₃ / acetonitrile / Heating

5: 1.) Hg(OAc)2, 2.) NaCl / 1.) acetone, water, r.t., 40 min, 2.) water, r.t., 21 h

6: NaBH(OAc)3 / acetic acid; acetonitrile / 0.67 h

7: proton-sponge, n-Bu₄NI / 48 h / 40 °C

8: NaOH / methanol / 1.5 h / Heating

With sodium hydroxide; oxalyl dichloride; Proton-Sponge; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; sodium chloride; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(96)02117-X

Reference yield:

methyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-phenylmethylene-α-D-glucopyranoside (199918-03-1) → (1S,2S,3S,4S,5R,6S)-3-Benzyloxy-2,6-bis-benzyloxymethoxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol (186541-50-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 25 percent / DIBAL-H

2: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.75 h / -78 - 20 °C

3: K₂CO₃ / acetonitrile / Heating

4: 1.) Hg(OAc)2, 2.) NaCl / 1.) acetone, water, r.t., 40 min, 2.) water, r.t., 21 h

5: NaBH(OAc)3 / acetic acid; acetonitrile / 0.67 h

6: proton-sponge, n-Bu₄NI / 48 h / 40 °C

7: NaOH / methanol / 1.5 h / Heating

With sodium hydroxide; oxalyl dichloride; Proton-Sponge; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; sodium chloride; In methanol; dichloromethane; acetic acid; acetonitrile;

DOI:10.1016/S0040-4039(96)02117-X

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → (1S,2S,3S,4S,5R,6S)-3-Benzyloxy-2,6-bis-benzyloxymethoxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol (186541-50-4)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH / dimethylformamide / 50 °C

2: 25 percent / DIBAL-H

3: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1.75 h / -78 - 20 °C

4: K₂CO₃ / acetonitrile / Heating

5: 1.) Hg(OAc)2, 2.) NaCl / 1.) acetone, water, r.t., 40 min, 2.) water, r.t., 21 h

6: NaBH(OAc)3 / acetic acid; acetonitrile / 0.67 h

7: proton-sponge, n-Bu₄NI / 48 h / 40 °C

8: NaOH / methanol / 1.5 h / Heating

With sodium hydroxide; oxalyl dichloride; Proton-Sponge; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; sodium chloride; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(96)02117-X

upstream raw materials:

Benzyloxymethyl chloride

benzyl bromide

methyl 4-O-benzyl-2,3-di-O-p-methoxybenzyl-α-D-glucopyranoside

p-methoxybenzyl chloride