(4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane

Base Information

• Chemical Name: (4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane
• CAS No.: 459426-98-3
• Molecular Formula: C₂₅H₃₄O₅
• Molecular Weight: 414.542

Synonyms:(4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane

Chemical Property of (4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane

There total 13 articles about (4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane 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: 85.0%

(R)-2-Benzyloxy-1-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol (459426-97-2) + methyl iodide (74-88-4) → (4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane (459426-98-3)

Guidance literature:

(R)-2-Benzyloxy-1-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol; With sodium hydride; In tetrahydrofuran; Heating;

methyl iodide; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(02)00500-2

Reference yield:

methyl ribofuranoside (1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7) → (4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane (459426-98-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: H₂SO₄ / 0 - 20 °C

2.1: NaIO₄; RuO₂*H₂O / acetonitrile; CCl₄; H₂O

3.1: K₂CO₃ / dimethylformamide / 20 °C

4.1: 92 percent / diethyl ether / Heating

5.1: 92 percent / t-Bu₄NI; NaH / tetrahydrofuran / Heating

6.1: HCl / dioxane; H₂O / 60 °C

7.1: H₂SO₄ / 0 °C

8.1: 84 percent / LiAlH₄ / tetrahydrofuran / 0 °C

9.1: 98 percent / NaH / tetrahydrofuran / 20 °C

10.1: 85 percent / (COCl)2; Et₃N / CH₂Cl₂; dimethylsulfoxide

11.1: 72 percent / K-Selectride / toluene / 0 - 20 °C

12.1: NaH / tetrahydrofuran / Heating

12.2: 85 percent / tetrahydrofuran / 20 °C

With hydrogenchloride; ruthenium(IV) oxide; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; tetra(tert-butyl)ammonium iodide; sodium hydride; potassium tri-sec-butyl-borohydride; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 10.1: Swern-oxidation;

DOI:10.1016/S0040-4039(02)00500-2

Reference yield:

methyl 2,3-O-isopropylidene-D-ribofuranoside (4099-85-8,5531-21-5,20672-63-3,20672-65-5,58763-00-1,63029-07-2,72402-14-3,84894-45-1,129263-68-9,828937-29-7) → (4S,5S)-4-((R)-2-Benzyloxy-1-methoxy-2-methyl-propyl)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane (459426-98-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaIO₄; RuO₂*H₂O / acetonitrile; CCl₄; H₂O

2.1: K₂CO₃ / dimethylformamide / 20 °C

3.1: 92 percent / diethyl ether / Heating

4.1: 92 percent / t-Bu₄NI; NaH / tetrahydrofuran / Heating

5.1: HCl / dioxane; H₂O / 60 °C

6.1: H₂SO₄ / 0 °C

7.1: 84 percent / LiAlH₄ / tetrahydrofuran / 0 °C

8.1: 98 percent / NaH / tetrahydrofuran / 20 °C

9.1: 85 percent / (COCl)2; Et₃N / CH₂Cl₂; dimethylsulfoxide

10.1: 72 percent / K-Selectride / toluene / 0 - 20 °C

11.1: NaH / tetrahydrofuran / Heating

11.2: 85 percent / tetrahydrofuran / 20 °C

With hydrogenchloride; ruthenium(IV) oxide; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; tetra(tert-butyl)ammonium iodide; sodium hydride; potassium tri-sec-butyl-borohydride; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 9.1: Swern-oxidation;

DOI:10.1016/S0040-4039(02)00500-2

upstream raw materials:

(R)-2-Benzyloxy-1-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol

methyl iodide

methyl ribofuranoside

methyl 2,3-O-isopropylidene-D-ribofuranoside

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