(2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol

Base Information

Chemical Name:(2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol
CAS No.:312493-72-4
Molecular Formula:C₃₁H₃₈O₆
Molecular Weight:506.639
Hs Code.:

Synonyms:(2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol

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Chemical Property of (2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol

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Technology Process of (2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol

There total 28 articles about (2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol 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: 95.0%

: Acetic acid (2S,4S,4aR,6S,7R,8aS,9aR,10aR)-2-(2-acetoxy-allyl)-6-benzyloxy-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-yl ester

: 312493-72-4
(2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol

Guidance literature:: With potassium carbonate; In methanol; at 25 ℃;
DOI:10.1016/S0040-4039(00)01339-3

Reference yield: 85.0%

: Acetic acid 1-[(2R,4aR,6S,7R,8aS,9aR,10aR)-6-benzyloxy-4a-methyl-4-oxo-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-2-ylmethyl]-vinyl ester

: 312493-72-4
(2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(00)01339-3

Reference yield:

: 312493-66-6
(4aS,6S,7R,8aS,9aR,10aR)-2,2,4a-Trimethyl-7-((E)-styryl)-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

: 312493-72-4
(2R,4S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-2-(2-hydroxymethyl-allyl)-4a-methyl-7-((E)-styryl)-decahydro-1,8,10-trioxa-anthracen-4-ol

Guidance literature:: Multi-step reaction with 14 steps

1: 96 percent / n-Bu₄NBr; NaH / tetrahydrofuran / 0 - 25 °C

2: 94 percent / CSA / methanol / 25 °C

3: 2,4,6-collidine / CH₂Cl₂ / -78 °C

4: 2,6-lutidine / CH₂Cl₂ / 0 °C

5: K₂CO₃ / methanol / 25 °C

6: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

7: tetrahydrofuran / -78 °C

8: 98 percent / TBAF / tetrahydrofuran / 25 °C

9: OsO₄; NMO / H₂O; 2-methyl-propan-2-ol / 25 °C

10: NaIO₄ / H₂O; tetrahydrofuran / 25 °C

11: 75 percent / Dowex (50W-X₂) / 25 °C

12: 82 percent / TMSOTf / acetonitrile / 0 °C

13: 80 percent / PCC; MS-4 Angstroem / benzene / 80 °C

14: 85 percent / L-Selectride / tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; trimethylsilyl trifluoromethanesulfonate; MS-4 Angstroem; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; L-Selectride; sodium hydride; potassium carbonate; pyridinium chlorochromate; Dowex (50W-X₂); camphor-10-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene; 1: Alkylation / 2: Hydrolysis / 3: Acetylation / 4: silylation / 5: Hydrolysis / 6: Oxidation / 7: Grignard reaction / 8: ether cleavage / 9: Oxidation / 10: Oxidation / 11: Etherification / 12: Substitution / 13: Oxidation / 14: Reduction;
DOI:10.1016/S0040-4039(00)01339-3