(1R,2S,4aS,10aR)-1-Benzyloxymethyl-2-hydroxymethyl-7-isopropyl-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol

Base Information

• Chemical Name: (1R,2S,4aS,10aR)-1-Benzyloxymethyl-2-hydroxymethyl-7-isopropyl-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol
• CAS No.: 74654-69-6
• Molecular Formula: C₂₇H₃₆O₄
• Molecular Weight: 424.58
• Mol file: 74654-69-6.mol

Synonyms:(1R,2S,4aS,10aR)-1-Benzyloxymethyl-2-hydroxymethyl-7-isopropyl-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol

Chemical Property of (1R,2S,4aS,10aR)-1-Benzyloxymethyl-2-hydroxymethyl-7-isopropyl-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,2S,4aS,10aR)-1-Benzyloxymethyl-2-hydroxymethyl-7-isopropyl-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol

There total 1 articles about (1R,2S,4aS,10aR)-1-Benzyloxymethyl-2-hydroxymethyl-7-isopropyl-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol 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:

(1R,2S,4aS,10aR)-1-Benzyloxymethyl-7-isopropyl-2-(2-methoxy-propoxymethyl)-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol → (1R,2S,4aS,10aR)-1-Benzyloxymethyl-2-hydroxymethyl-7-isopropyl-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol (74654-69-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; Yield given;

DOI:10.1021/ja00536a065

Reference yield:

(1R,2S,4aS,10aR)-1-Benzyloxymethyl-2-hydroxymethyl-7-isopropyl-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol (74654-69-6) → l-triptonide (38647-11-9)

Guidance literature:

Multi-step reaction with 11 steps

1: acetic acid

2: pyridine / 20 °C

3: hydrochloric acid / methanol / 20 °C

4: CrO₃, pyridine*HCl / CH₂Cl₂ / 20 °C

5: 1.) o-C₆H₄(NH₂)2, PhCO₂H, 2.) hydrochloric acid / 1.) ethanol, 20 deg C, 2.) 20 deg C

6: NaClO₂, HOSO₂NH₂ / dioxane; H₂O / 20 °C

7: hydrogen / Pd-C / ethanol / 20 °C

8: CrO₃ / acetic acid; H₂O / 40 °C

9: 1.) KOH, 2.) NaBH₄ / 1.) methanol, water, 20 deg C, 2.) ethanol, 20 deg C

10: NaIO₄ / methanol; H₂O / 20 °C

11: 1.) H₂O₂, KOH, 2.) 3,5-(NO₂)2C₆H₃CO₃H, Na₂HPO₄ / 1.) methanol, 20 deg C, 2.) CH₂Cl₂, 20 deg C

With pyridine; chromium(VI) oxide; hydrogenchloride; potassium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; amidosulfuric acid fluoride; 3,5-dinitrobenzoperoxoic acid; hydrogen; dihydrogen peroxide; pyridine hydrochloride; 1,2-diamino-benzene; benzoic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetic acid;

DOI:10.1021/ja00536a065

Reference yield:

(1R,2S,4aS,10aR)-1-Benzyloxymethyl-2-hydroxymethyl-7-isopropyl-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1,8-diol (74654-69-6) → Acetic acid (4bS,7S,8R,8aR)-8-benzyloxymethyl-8-hydroxy-7-hydroxymethyl-2-isopropyl-4b-methyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-1-yl ester

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid

2: pyridine / 20 °C

3: hydrochloric acid / methanol / 20 °C

With pyridine; hydrogenchloride; In methanol; acetic acid;

DOI:10.1021/ja00536a065

Downstream raw materials:

Acetic acid (4bS,8aR)-8-benzyloxymethyl-7-formyl-2-isopropyl-4b-methyl-4b,5,6,8a,9,10-hexahydro-phenanthren-1-yl ester

Acetic acid (4bS,7R,8R,8aR)-8-benzyloxymethyl-7-formyl-8-hydroxy-2-isopropyl-4b-methyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-1-yl ester

l-triptonide