(2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone
CAS No.:136892-47-2
Molecular Formula:C₂₈H₃₀O₆
Molecular Weight:462.543
Hs Code.:

Synonyms:(2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone

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Chemical Property of (2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone

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Technology Process of (2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone

There total 6 articles about (2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone 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: 70.0%

: 134680-58-3
(3aR,4R,5S,6R,7S)-5,6,7-Tris-benzyloxy-3,3a,4,5,6,7-hexahydro-benzo[c]isoxazol-4-ol

: 136892-47-2
(2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone

: 134680-59-4
(2R,3S,4S,5R,6S)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone

Guidance literature:: With hydrogen; acetic acid; Raney-Ni-W₄; In 1,4-dioxane; water; at 25 ℃; for 4h; under 760 Torr;
DOI:10.1016/0008-6215(91)89017-A

Reference yield:

: 4356-80-3,34212-64-1,40653-32-5,53008-65-4,68027-27-0,73111-53-2,128184-63-4,138794-99-7,55094-38-7,641635-63-4
methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside

: 136892-47-2
(2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone

Guidance literature:: Multi-step reaction with 6 steps

1: 1) oxalyl chloride, DMSO, 2) NET₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2a) -78 deg C, 15 min, 2b) -78 to -40 deg C

2: 91 percent / benzene / 0.17 h / 25 °C

3: 1) Ac₂O, conc. H₂SO₄, 2) NaOMe / 1) 0 deg C, 10 min, 2a) MeOH, 0 deg c, 10 min, 2b) 25 deg C, 0.5h

4: 100 percent / H₂NNH₂*HCl, pyridine / 3 h / 25 °C

5: 75 percent / 5percent aq. NaOCl / toluene / 0.5 h / 100 °C

6: 28 percent / H₂, HOAc / Raney-Ni-W₄ / H₂O; dioxane / 4 h / 25 °C / 760 Torr

With pyridine; sodium hypochlorite; oxalyl dichloride; hydrazine hydrochloride; sulfuric acid; hydrogen; sodium methylate; acetic anhydride; acetic acid; dimethyl sulfoxide; triethylamine; Raney-Ni-W₄; In 1,4-dioxane; water; toluene; benzene;
DOI:10.1016/0008-6215(91)89017-A

Reference yield:

: 139285-93-1
(2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal

: 136892-47-2
(2R,3S,4S,5R,6R)-2,3,4-Tris-benzyloxy-5-hydroxy-6-hydroxymethyl-cyclohexanone

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / H₂NNH₂*HCl, pyridine / 3 h / 25 °C

2: 75 percent / 5percent aq. NaOCl / toluene / 0.5 h / 100 °C

3: 28 percent / H₂, HOAc / Raney-Ni-W₄ / H₂O; dioxane / 4 h / 25 °C / 760 Torr

With pyridine; sodium hypochlorite; hydrazine hydrochloride; hydrogen; acetic acid; Raney-Ni-W₄; In 1,4-dioxane; water; toluene;
DOI:10.1016/0008-6215(91)89017-A