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

Base Information

Chemical Name:(1S,2S,3R,4S,5S,6S)-2,3,6-Tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol
CAS No.:187980-39-8
Molecular Formula:C₄₃H₄₆O₈
Molecular Weight:690.833
Hs Code.:

Synonyms:(1S,2S,3R,4S,5S,6S)-2,3,6-Tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

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

Chemical Property:

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

There total 23 articles about (1S,2S,3R,4S,5S,6S)-2,3,6-Tris-benzyloxy-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:

: 187980-19-4
1D-1-O-allyl-2,5,6-tri-O-benzyl-3,4-di-O-p-methoxybenzyl-myo-inositol

: 187980-39-8
(1S,2S,3R,4S,5S,6S)-2,3,6-Tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Guidance literature:: Multi-step reaction with 2 steps

1: DABCO / RhCl(PPh₃)3 / ethanol / 6 h / Heating

2: 1.93 g / aq. HCl / acetone / 0.5 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; RhCl(PPh₃)3; In ethanol; acetone; 1: Isomerization / 2: Hydrolysis;
DOI:10.1021/ol991188y

Reference yield:

: 642-38-6
quebrachitol

: 187980-39-8
(1S,2S,3R,4S,5S,6S)-2,3,6-Tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Guidance literature:: Multi-step reaction with 16 steps

1.1: 91 percent / CSA / dimethylformamide / 5 h / 20 - 60 °C

2.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

3.1: 42 g / BBr₃ / CH₂Cl₂ / 12 h / 20 °C

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

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

6.1: 2.46 g / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

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

8.1: 2.15 g / NaBH₄ / methanol / 1 h / 5 °C

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

10.1: 2.1 g / AcCl; MeOH / CH₂Cl₂

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

12.1: 1.6 g / conc. HCl / methanol

13.1: Bu₂SnO / toluene / 2 h / Heating

13.2: CsF / dimethylformamide / 18 h / 20 °C

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

15.1: DABCO / RhCl(PPh₃)3 / ethanol / 6 h / Heating

16.1: 1.93 g / aq. HCl / acetone / 0.5 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; methanol; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron tribromide; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; RhCl(PPh₃)3; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Cyclization / 2.1: mesylation / 3.1: Ring cleavage / 4.1: Cyclization / 5.1: Etherification / 6.1: Reduction / 7.1: Swern oxidation / 8.1: Reduction / 9.1: Etherification / 10.1: Hydrolysis / 11.1: Etherification / 12.1: Hydrolysis / 13.1: Cyclization / 13.2: Substitution / 14.1: Etherification / 15.1: Isomerization / 16.1: Hydrolysis;
DOI:10.1021/ol991188y

Reference yield:

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

: 187980-39-8
(1S,2S,3R,4S,5S,6S)-2,3,6-Tris-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclohexanol

Guidance literature:: Multi-step reaction with 15 steps

1.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

2.1: 42 g / BBr₃ / CH₂Cl₂ / 12 h / 20 °C

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

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

5.1: 2.46 g / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

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

7.1: 2.15 g / NaBH₄ / methanol / 1 h / 5 °C

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

9.1: 2.1 g / AcCl; MeOH / CH₂Cl₂

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

11.1: 1.6 g / conc. HCl / methanol

12.1: Bu₂SnO / toluene / 2 h / Heating

12.2: CsF / dimethylformamide / 18 h / 20 °C

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

14.1: DABCO / RhCl(PPh₃)3 / ethanol / 6 h / Heating

15.1: 1.93 g / aq. HCl / acetone / 0.5 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; methanol; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron tribromide; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; RhCl(PPh₃)3; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: mesylation / 2.1: Ring cleavage / 3.1: Cyclization / 4.1: Etherification / 5.1: Reduction / 6.1: Swern oxidation / 7.1: Reduction / 8.1: Etherification / 9.1: Hydrolysis / 10.1: Etherification / 11.1: Hydrolysis / 12.1: Cyclization / 12.2: Substitution / 13.1: Etherification / 14.1: Isomerization / 15.1: Hydrolysis;
DOI:10.1021/ol991188y