(1S,2R,3S,4R,5R,6S)-3,4-Bis-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

Base Information

Chemical Name:(1S,2R,3S,4R,5R,6S)-3,4-Bis-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol
CAS No.:116180-58-6
Molecular Formula:C₃₆H₄₀O₈
Molecular Weight:600.709
Hs Code.:

Synonyms:(1S,2R,3S,4R,5R,6S)-3,4-Bis-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

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Chemical Property of (1S,2R,3S,4R,5R,6S)-3,4-Bis-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

Chemical Property:

Purity/Quality:

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Hazard Codes:

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Useful:

Technology Process of (1S,2R,3S,4R,5R,6S)-3,4-Bis-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

There total 33 articles about (1S,2R,3S,4R,5R,6S)-3,4-Bis-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol 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:

: 3,4-di-O-(4-methoxybenzyl)-5,6-di-O-benzyl-1,2-O-cyclohexylidene-myoinositol

: 114342-82-4,116180-56-4,116180-58-6
3,4-di-O-(4-methoxybenzyl)-5,6-di-O-benzyl-myoinositol

Guidance literature:: With hydrogenchloride; In methanol;

Reference yield:

: 642-38-6
quebrachitol

: 116180-58-6
(1S,2R,3S,4R,5R,6S)-3,4-Bis-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 12 steps

1: 91 percent / CSA / dimethylformamide / 5 h / 20 - 60 °C

2: Et₃N / CH₂Cl₂ / 1 h / 20 °C

3: 42 g / BBr₃ / CH₂Cl₂ / 12 h / 20 °C

4: CSA / dimethylformamide / 4 h / 80 °C

5: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

6: 2.46 g / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

7: oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / -60 °C

8: 2.15 g / NaBH₄ / methanol / 1 h / 5 °C

9: NaH; PMBCl / Bu₄NI / dimethylformamide / 4 h / 0 °C

10: 2.1 g / AcCl; MeOH / CH₂Cl₂

11: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

12: 1.6 g / conc. HCl / methanol

With hydrogenchloride; methanol; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron tribromide; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Cyclization / 2: mesylation / 3: Ring cleavage / 4: Cyclization / 5: Etherification / 6: Reduction / 7: Swern oxidation / 8: Reduction / 9: Etherification / 10: Hydrolysis / 11: Etherification / 12: Hydrolysis;
DOI:10.1021/ol991188y

Reference yield:

: 58769-23-6
1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol

: 116180-58-6
(1S,2R,3S,4R,5R,6S)-3,4-Bis-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 11 steps

1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: 42 g / BBr₃ / CH₂Cl₂ / 12 h / 20 °C

3: CSA / dimethylformamide / 4 h / 80 °C

4: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

5: 2.46 g / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

6: oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / -60 °C

7: 2.15 g / NaBH₄ / methanol / 1 h / 5 °C

8: NaH; PMBCl / Bu₄NI / dimethylformamide / 4 h / 0 °C

9: 2.1 g / AcCl; MeOH / CH₂Cl₂

10: NaH / Bu₄NI / dimethylformamide / 4 h / 0 °C

11: 1.6 g / conc. HCl / methanol

With hydrogenchloride; methanol; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron tribromide; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: mesylation / 2: Ring cleavage / 3: Cyclization / 4: Etherification / 5: Reduction / 6: Swern oxidation / 7: Reduction / 8: Etherification / 9: Hydrolysis / 10: Etherification / 11: Hydrolysis;
DOI:10.1021/ol991188y