(1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane

Base Information

• Chemical Name: (1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane
• CAS No.: 128329-71-5
• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.418
• Mol file: 128329-71-5.mol

Synonyms:(1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane

Chemical Property of (1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane

There total 9 articles about (1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane 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:

(1'R,4R,5S)-4-(2'-(benzyloxy)-1'-methylethyl)-6-((diphenyl-tert-butylsiloxy)methyl)-2,2,5-trimethyl-1,3-dioxane (128329-70-4,128440-46-0) → (1'R,4R,5S,6S)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane (128440-47-1) + (1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane (128329-71-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 10h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00169a042

Reference yield:

(S)-3-benzyloxy-2-methylpropan-1-ol (63930-46-1) → (1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane (128329-71-5)

Guidance literature:

Multi-step reaction with 9 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

2: 1.) triethylamine, di-n-butylboryl triflate / 1.) CH₂Cl₂, from -78 deg C to 0 deg C, 50 min, 2.) -78 deg C, 18 h

3: 1.) tri-n-butylborane, glacial acetic acid, 2.) lithium borohydride / 1.) THF, 25 deg C, 1.5 h, 2a.) 0 deg C, 1.5 h, 2b.) 25 deg C, 30 min

4: 0.908 g / pyridine / 18 h / 5 °C

5: 0.468 g / lithium triethylborohydride / tetrahydrofuran / 24 h / 25 °C

6: 1.30 g / N-methylmorpholine N-oxide monohydrate, 0.16 M aq. osmium tetraoxide / acetone / 10 h / 25 °C

7: 2.01 g / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 25 °C

8: 2.13 g / 2,2-dimethoxypropane, d,l-camphorsulfonic acid / 2 h / 25 °C

9: 1 N Bu₄NF / tetrahydrofuran / 10 h / 25 °C

With pyridine; dmap; osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; tributyl borane; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; lithium triethylborohydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 2,2-dimethoxy-propane; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ja00169a042

Reference yield:

(3R,4S)-1-(benzyloxy)-3-hydroxy-4-(hydroxymethyl)-2-methyl-5-hexene (73814-77-4,108814-34-2) → (1'R,4R,5S,6R)-4-(2'-(benzyloxy)-1'-methylethyl)-6-(hydroxymethyl)-2,2,5-trimethyl-1,3-dioxane (128329-71-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 0.908 g / pyridine / 18 h / 5 °C

2: 0.468 g / lithium triethylborohydride / tetrahydrofuran / 24 h / 25 °C

3: 1.30 g / N-methylmorpholine N-oxide monohydrate, 0.16 M aq. osmium tetraoxide / acetone / 10 h / 25 °C

4: 2.01 g / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 25 °C

5: 2.13 g / 2,2-dimethoxypropane, d,l-camphorsulfonic acid / 2 h / 25 °C

6: 1 N Bu₄NF / tetrahydrofuran / 10 h / 25 °C

With pyridine; dmap; osmium(VIII) oxide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; lithium triethylborohydride; 4-methylmorpholine N-oxide; triethylamine; 2,2-dimethoxy-propane; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ja00169a042

upstream raw materials:

(1'R,4R,5S)-4-(2'-(benzyloxy)-1'-methylethyl)-6-((diphenyl-tert-butylsiloxy)methyl)-2,2,5-trimethyl-1,3-dioxane

(S)-3-benzyloxy-2-methylpropan-1-ol

(3R,4S)-1-(benzyloxy)-3-hydroxy-4-(hydroxymethyl)-2-methyl-5-hexene

(S)-3-((R)-3-Benzyloxy-2-methyl-propionyl)-4-isopropyl-oxazolidin-2-one

Downstream raw materials:

(R)-1-{(2R,5S,2'S,5'R)-5'-[(4S,5S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-ethanol

(R)-1-{(2R,5S,2'S,5'S)-5'-[(4S,5S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl]-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl}-ethanol

C₆₁H₉₆O₁₀SSi₂

(2R,4R,8R,9R,10S,11S,12(2S,5S(2R,5S(R))))-1-((1,1-dimethylethyl)diphenylsiloxy)-9,11-((1-methylethylidene)dioxy)-2,4,8,10-tetramethyl-12-(tetrahydro-5-methyl-5-(tetrahydro-5-(1-((1,1-dimethylethyl)dimethylsiloxy)ethyl)-5-methyl-2-furanyl)-2-furanyl)-...