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

Base Information

• Chemical Name: (1S,2S,3R,4S,5S,6R)-3-Benzyloxy-5-benzyloxymethoxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol
• CAS No.: 1053256-80-6
• Molecular Formula: C₂₉H₃₄O₈
• Molecular Weight: 510.584
• Mol file: 1053256-80-6.mol

Synonyms:(1S,2S,3R,4S,5S,6R)-3-Benzyloxy-5-benzyloxymethoxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (1S,2S,3R,4S,5S,6R)-3-Benzyloxy-5-benzyloxymethoxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol 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: 74.0%

C50H46O11 → (1S,2S,3R,4S,5S,6R)-3-Benzyloxy-5-benzyloxymethoxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol (1053256-80-6)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 50 ℃; for 24h;

DOI:10.1021/jo00088a003

Reference yield:

quebrachitol (642-38-6) → (1S,2S,3R,4S,5S,6R)-3-Benzyloxy-5-benzyloxymethoxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol (1053256-80-6)

Guidance literature:

Multi-step reaction with 15 steps

1: 81 percent / camphorsulfonic acid / dimethylformamide / 5 h / 70 °C

2: 92 percent / TEA / CH₂Cl₂ / 2 h / 0 °C

3: 82 percent / BBr₃ / CH₂Cl₂ / Ambient temperature

4: camphorsulfonic acid / dimethylformamide / 5 h / 70 °C

5: 99 percent / NaH / dimethylformamide / 0 °C

6: 82 percent / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

7: 1.) (COCl)2, DMSO, 2.) diisopropylamine / 1.) CH₂Cl₂, 2.) -78 deg C to -10 deg C

8: LiBH₄ / tetrahydrofuran / -78 °C

9: 92 percent / NaH / dimethylformamide / 7 h

10: 73 percent / AcCl / CH₂Cl₂; methanol / 0.25 h / Ambient temperature

11: pyridine / Ambient temperature

12: 84 percent / conc. HCl / CH₂Cl₂; methanol / 9 h / Ambient temperature

13: 95 percent / pyridine

14: 89 percent / (i-Pr)2NEt / 48 h / 62 °C

15: 74 percent / MeONa / methanol; tetrahydrofuran / 24 h / 50 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; lithium borohydride; oxalyl dichloride; TEA; camphor-10-sulfonic acid; sodium methylate; boron tribromide; sodium hydride; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00088a003

Reference yield:

Methanesulfonic acid (3aS,4S,5S,5aS,8aR,8bS)-5-methoxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (134182-86-8) → (1S,2S,3R,4S,5S,6R)-3-Benzyloxy-5-benzyloxymethoxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol (1053256-80-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 82 percent / BBr₃ / CH₂Cl₂ / Ambient temperature

2: camphorsulfonic acid / dimethylformamide / 5 h / 70 °C

3: 99 percent / NaH / dimethylformamide / 0 °C

4: 82 percent / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

5: 1.) (COCl)2, DMSO, 2.) diisopropylamine / 1.) CH₂Cl₂, 2.) -78 deg C to -10 deg C

6: LiBH₄ / tetrahydrofuran / -78 °C

7: 92 percent / NaH / dimethylformamide / 7 h

8: 73 percent / AcCl / CH₂Cl₂; methanol / 0.25 h / Ambient temperature

9: pyridine / Ambient temperature

10: 84 percent / conc. HCl / CH₂Cl₂; methanol / 9 h / Ambient temperature

11: 95 percent / pyridine

12: 89 percent / (i-Pr)2NEt / 48 h / 62 °C

13: 74 percent / MeONa / methanol; tetrahydrofuran / 24 h / 50 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; lithium borohydride; oxalyl dichloride; camphor-10-sulfonic acid; sodium methylate; boron tribromide; sodium hydride; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00088a003

upstream raw materials:

quebrachitol

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol

Methanesulfonic acid (3aS,4S,5S,5aS,8aR,8bS)-5-methoxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester

Methanesulfonic acid (3aS,4S,5S,5aS,8aR,8bS)-5-hydroxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester