((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol

Base Information

• Chemical Name: ((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol
• CAS No.: 1453285-73-8
• Molecular Formula: C₂₂H₂₈O₄
• Molecular Weight: 356.462
• Mol file: 1453285-73-8.mol

Synonyms:((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol

Chemical Property of ((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol

There total 8 articles about ((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol 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:

C23H32O7S → ((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol (1453285-73-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 6h;

DOI:10.1016/j.tet.2013.07.072

Reference yield:

C26H36O7S → ((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol (1453285-73-8)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; toluene-4-sulfonic acid / 3 h / 20 °C

2: sodium hydride / tetrahydrofuran; mineral oil / 6 h / 0 - 20 °C

With methanol; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; mineral oil;

DOI:10.1016/j.tet.2013.07.072

Reference yield:

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane (87604-53-3) → ((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol (1453285-73-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: ozone / dichloromethane / -78 °C

1.2: 2 h / 0 °C

2.1: benzene / 2 h / 20 °C

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 °C

4.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

4.2: 12 h / -20 °C / Molecular sieve

5.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 12 h / 0 - 20 °C

6.1: copper(l) iodide / diethyl ether / 0.5 h / -23 °C

6.2: 4 h / -40 °C

7.1: triethylamine / dichloromethane / 1 h / 0 °C

8.1: methanol; toluene-4-sulfonic acid / 3 h / 20 °C

9.1: sodium hydride / tetrahydrofuran; mineral oil / 6 h / 0 - 20 °C

With titanium(IV) isopropylate; methanol; copper(l) iodide; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; mineral oil; benzene; 2.1: |Wittig Olefination / 4.1: |Sharpless Asymmetric Epoxidation / 4.2: |Sharpless Asymmetric Epoxidation;

DOI:10.1016/j.tet.2013.07.072

upstream raw materials:

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

5-O-benzyl-2,3,4-trideoxy-6,7-O-isopropylidene-D-erythro-hept-2-enoic acid ethyl ester

(S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

Downstream raw materials:

(((2R,3S,5S,6R)-3-(benzyloxy)-6-((benzyloxy)methyl)-5-methyltetrahydro-2H-pyran-2-yl)methoxy)(tert-butyl)dimethylsilane