(1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol

Base Information

Chemical Name:(1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol
CAS No.:479669-02-8
Molecular Formula:C₃₈H₄₄O₆
Molecular Weight:596.764
Hs Code.:

Synonyms:(1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol

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Chemical Property of (1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol

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Technology Process of (1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol

There total 15 articles about (1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-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:

: (2S,3R,3aS,4S,5R,6S,7aR)-3a,6-Bis-benzyloxy-4,5-bis-benzyloxymethyl-5-methyl-octahydro-benzofuran-2,3-diol

: 479669-02-8
(1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol

Guidance literature:: (2S,3R,3aS,4S,5R,6S,7aR)-3a,6-Bis-benzyloxy-4,5-bis-benzyloxymethyl-5-methyl-octahydro-benzofuran-2,3-diol; With lead(IV) acetate; In dichloromethane; at 20 ℃;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0040-4039(02)02058-0

Reference yield:

: 322390-88-5
1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

: 479669-02-8
(1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol

Guidance literature:: Multi-step reaction with 13 steps

1.1: 83 percent / DMAP / CH₂Cl₂ / 20 °C

2.1: 75 percent / Bu₃SnH; AIBN / toluene / Heating

3.1: 78 percent / Na / liquid ammonia; tetrahydrofuran / -78 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

5.1: tetrahydrofuran / 0 °C

6.1: 100 percent / Et₃N / CH₂Cl₂ / 20 °C

7.1: 58 percent / benzoyl peroxide / 3 h / Heating

8.1: 72 percent / dimethylsulfoxide / 120 °C

9.1: 65 percent / O₃; NaHCO₃; Me₂S / CH₂Cl₂ / -78 - 20 °C

10.1: 100 percent / LiAlH₄ / tetrahydrofuran / 0 - 50 °C

11.1: 100 percent / Bu₄NI / dimethylformamide / 0 - 60 °C

12.1: aq. HCl / acetic acid; tetrahydrofuran / Heating

13.1: Pb(OAc)4 / CH₂Cl₂ / 20 °C

13.2: LiAlH₄ / tetrahydrofuran / 0 °C

With lead(IV) acetate; hydrogenchloride; dmap; lithium aluminium tetrahydride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; dibenzoyl peroxide; In tetrahydrofuran; dichloromethane; ammonia; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(02)02058-0

Reference yield:

: ((3aR,5R,6R,6aR)-6-Hydroxy-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetaldehyde

: 479669-02-8
(1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: tetrahydrofuran / 0 °C

2.1: 100 percent / Et₃N / CH₂Cl₂ / 20 °C

3.1: 58 percent / benzoyl peroxide / 3 h / Heating

4.1: 72 percent / dimethylsulfoxide / 120 °C

5.1: 65 percent / O₃; NaHCO₃; Me₂S / CH₂Cl₂ / -78 - 20 °C

6.1: 100 percent / LiAlH₄ / tetrahydrofuran / 0 - 50 °C

7.1: 100 percent / Bu₄NI / dimethylformamide / 0 - 60 °C

8.1: aq. HCl / acetic acid; tetrahydrofuran / Heating

9.1: Pb(OAc)4 / CH₂Cl₂ / 20 °C

9.2: LiAlH₄ / tetrahydrofuran / 0 °C

With lead(IV) acetate; hydrogenchloride; lithium aluminium tetrahydride; dimethylsulfide; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; ozone; triethylamine; dibenzoyl peroxide; In tetrahydrofuran; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)02058-0