(2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol
• CAS No.: 162601-88-9
• Molecular Formula: C₁₉H₃₀O₇
• Molecular Weight: 370.443
• Mol file: 162601-88-9.mol

Synonyms:(2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol

Chemical Property of (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol

There total 11 articles about (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol 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: 98.0%

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[(S)-3-((R)-4-acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester (521291-38-3) → (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol (162601-88-9)

Guidance literature:

With base;

DOI:10.1248/cpb.48.2017

Reference yield:

(3S,9S)-megastigma-6,7-diene-3,5,9-triol 9-O-β-D-glucopyranoside → Damascenon (23726-93-4) + 3-hydroxy-β-damascone (160550-79-8,56915-02-7) + (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol (162601-88-9)

Guidance literature:

In water; at 90 ℃; for 0.5h; pH=2.0;

DOI:10.1271/bbb.66.2692

Reference yield:

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol (118829-40-6,118829-45-1) → (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(S)-3-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-tetrahydro-pyran-3,4,5-triol (162601-88-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / DMAP; Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

2.1: BuLi / hexane; tetrahydrofuran / 0.25 h / -40 °C

2.2: hexane; tetrahydrofuran / 0.42 h / -40 - 20 °C

3.1: 4.82 g / MnO₂ / diethyl ether; hexane / 15 h / 20 °C

4.1: 99 percent / aq, HF / acetonitrile / 0.5 h / 20 °C

5.1: 96 percent / pyridine / 2 h / 20 °C

6.1: 100 percent / (1S,2S)-TsNHCH(Ph)CH(Ph)NHTs; iPrOH; KOH / [RuCl₂(p-cymene)]2 / 2 h / 20 °C

7.1: 95 percent / AgOTf; N,N'-tetramethylurea; molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / 0 - 20 °C

8.1: 98 percent / LiOH*H₂O / methanol / 20 h / 20 °C

With pyridine; dmap; manganese(IV) oxide; potassium hydroxide; lithium hydroxide; n-butyllithium; 4 A molecular sieve; hydrogen fluoride; silver trifluoromethanesulfonate; triethylamine; isopropyl alcohol; (1S,2S)-N,N'-bis((4-methylphenyl)sulfonyl)-1,2-diphenylethane-1,2-diamine; tetramethylurea; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile;

DOI:10.1039/b208758h

upstream raw materials:

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[(S)-3-((R)-4-acetoxy-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-prop-2-ynyloxy]-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol

1,1-dimethylethyl{[(1R)-4-ethynyl-3,5,5-trimethylcyclohex-3-entl]oxy}dimethylsilane