(4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane

Base Information

• Chemical Name: (4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane
• CAS No.: 112497-21-9
• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.364
• Mol file: 112497-21-9.mol

Synonyms:(4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane

Chemical Property of (4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane

There total 26 articles about (4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane 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: 90.0%

(3S,5S)-6-<(benzyloxy)methyl>-4-<1-(tert-butyldiphenylsilyloxy)ethyl>-2,2-dimethyl-1,3-dioxacyclohexane (112497-22-0) → (4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane (112497-21-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)92381-5

Reference yield: 50.0%

(E)-(S)-6-Benzyloxy-5-hydroxy-hex-2-enoic acid methyl ester (1067185-74-3) → (4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane (112497-21-9)

Guidance literature:

(E)-(S)-6-Benzyloxy-5-hydroxy-hex-2-enoic acid methyl ester; With chloro(acetato)mercury(II); ytterbium(III) triflate; In acetone; at 20 ℃; for 24h;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 24h; Further stages.;

DOI:10.1016/j.tetlet.2008.07.022

Reference yield:

(R)-benzyl glycidol (14618-80-5) → (4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane (112497-21-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) nBuLi, 2) BF₃*Et₂O / 1) THF, 2) THF

2: H₂ / Lindlar catalyst / ethanol / 760 Torr / Ambient temperature

3: tBuOOH, VO(acac)2 / toluene / -15 deg C to rt

4: nBu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

5: p-TsOH

6: 1) 9-BBN, 2) H₂O₂, NaOH / 1) THF

With tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; Lindlar's catalyst; In tetrahydrofuran; ethanol; toluene;

DOI:10.1016/S0040-4039(00)92213-5

upstream raw materials:

(4S,6R)-4-Benzyloxymethyl-2,2-dimethyl-6-vinyl-[1,3]dioxane

(3S,5S)-6-<(benzyloxy)methyl>-4-<1-(tert-butyldiphenylsilyloxy)ethyl>-2,2-dimethyl-1,3-dioxacyclohexane

<4R-(4α,5α)>-4-<(phenylmethoxy)methyl>-6-ethenyl-2,2-dimethyl-1,3-dioxane

2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol

Downstream raw materials:

((4S,6S)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)methanol

Trifluoro-methanesulfonic acid (4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl ester

(S)-((4R,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-(2-{(4S,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-[1,3]dithian-2-yl)-methanol

(4S,6R)-4-benzyloxymethyl-6-(2-iodoethyl)-2,2-dimethyl-1,3-dioxane