DL-(1,2/3,4,5)-1,2,3-tri-O-benzyl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

Base Information

• Chemical Name: DL-(1,2/3,4,5)-1,2,3-tri-O-benzyl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol
• CAS No.: 125258-11-9
• Molecular Formula: C₂₈H₃₂O₅
• Molecular Weight: 448.559
• Mol file: 125258-11-9.mol

Synonyms:

Chemical Property of DL-(1,2/3,4,5)-1,2,3-tri-O-benzyl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DL-(1,2/3,4,5)-1,2,3-tri-O-benzyl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

There total 55 articles about DL-(1,2/3,4,5)-1,2,3-tri-O-benzyl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol 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: 97.0%

(1RS,6RS,8RS,9SR,10SR)-8,9,10-trobenzyloxy-3,3-dimethyl-2,4-dioxabicyclo<4.4.0>decane (117902-49-5) → DL-(1,2/3,4,5)-1,2,3-tri-O-benzyl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol (125258-11-9,125354-35-0)

Guidance literature:

With acetic acid; In ethanol; water; for 3.5h; Ambient temperature;

DOI:10.1016/0008-6215(89)85057-8

Reference yield: 95.0%

DL-(1,2,4/3,5)-4-O-benzoyl-5-benzoyloxymethyl-1,2,3-tri-O-benzyl-1,2,3,4-cyclohexanetetrol (125258-19-7) → DL-(1,2,4/3,5)-1,2,3-tri-O-benzyl-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol (125258-11-9,125354-35-0)

Guidance literature:

With sodium methylate; In methanol; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(89)85057-8

Reference yield:

benzyl bromide (100-39-0) → (1R,2R,3R,4S,6R)-2,3,4-Tris-benzyloxy-6-hydroxymethyl-cyclohexanol (125258-11-9,125354-35-0)

Guidance literature:

Multi-step reaction with 11 steps

1: NaH / dimethylformamide / Ambient temperature

2: p-toluenesulfonic acid monohydrate / ethyl acetate; methanol / Ambient temperature

3: 98 percent / imidazole / dimethylformamide / Ambient temperature

4: mercury(II) chloride, calcium carbonate / acetonitrile; H₂O / 0.5 h / Ambient temperature

5: 1.) triethylamine, 2.) acetic anhydride / 1.) pyridine, 30 h, RT, 2.) 40 h, RT

6: H₂ / Raney nickel T-4 / ethanol / 1 h / 760 Torr / Ambient temperature

7: tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / Ambient temperature

8: 1.) pyridinium chlorochromate, molecular sieves 2.) pyridine / 1.) RT, 1 h, 2.) RT, 4 d

9: 50 percent / NaCl / H₂O; dimethylsulfoxide / 1 h / 120 - 170 °C

10: 88 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / -15 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; molecular sieve; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; calcium carbonate; sodium chloride; mercury dichloride; Raney nickel T-4; In tetrahydrofuran; methanol; ethanol; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00386a011

upstream raw materials:

(4aR,6S,7S,8S,8aR)-6,7,8-Tris-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxine

DL-(1,2,4/3,5)-4-O-benzoyl-5-benzoyloxymethyl-1,2,3-tri-O-benzyl-1,2,3,4-cyclohexanetetrol

DL-(1,2/3,4,5)-1,2,3-tri-O-benzyl-4-O-methanesulfonyl-5-methanesulfonyloxymethyl-1,2,3,4-cyclohexanetetrol

Benzoic acid (1S,2R,3S,4R,5R)-3,4,5-tris-benzyloxy-2-methanesulfonyloxy-cyclohexylmethyl ester

Downstream raw materials:

(1S,2S,3S,4R,5R)-1,2,3,4-tetraacetoxy-5-acetoxymethylcyclohexane

(1S,2S,3S,4R,5R)-pseudo-α-D-glucose

(1S,2S,3S,4S,5S)-pseudo-β-L-altrose

(1S,2S,3S,4S,5S)-5-(acetoxymethyl)cyclohexane-1,2,3,4-tetrayl tetraacetate