(S)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol

Base Information

• Chemical Name: (S)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol
• CAS No.: 94059-73-1
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• Mol file: 94059-73-1.mol

Synonyms:(S)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol

Chemical Property of (S)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol

There total 5 articles about (S)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol 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: 63.0%

(2R,3R,6S)-3-Benzyloxy-3-methyl-2-[(S)-1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,7-dioxa-spiro[5.5]undecane (94059-72-0) → (S)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol (94059-73-1)

Guidance literature:

With hydrogenchloride; water; In 1,2-dimethoxyethane; r.t., 1 h then 50 deg C, 45 min;

DOI:10.1139/v84-496

Reference yield:

(2R,3R,6S)-2-((S)-2-Hydroxy-1-methyl-ethyl)-3-methyl-1,7-dioxa-spiro[5.5]undecan-3-ol (94059-70-8) → (S)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol (94059-73-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4.5 h

2: 68 percent / 50 percent NaH in oil / dimethylformamide / 2 h / 55 °C

3: 63 percent / H₂O, 1 N HCl / 1,2-dimethoxy-ethane / r.t., 1 h then 50 deg C, 45 min

With hydrogenchloride; water; pyridinium p-toluenesulfonate; sodium hydride; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1139/v84-496

Reference yield:

(2R,3R,6S)-3-Methyl-2-[(S)-1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,7-dioxa-spiro[5.5]undecan-3-ol (94059-71-9) → (S)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol (94059-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / 50 percent NaH in oil / dimethylformamide / 2 h / 55 °C

2: 63 percent / H₂O, 1 N HCl / 1,2-dimethoxy-ethane / r.t., 1 h then 50 deg C, 45 min

With hydrogenchloride; water; sodium hydride; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1139/v84-496

upstream raw materials:

(2R,3R,6S)-3-Benzyloxy-3-methyl-2-[(S)-1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,7-dioxa-spiro[5.5]undecane

(2R,3R,6S)-2-((S)-2-Hydroxy-1-methyl-ethyl)-3-methyl-1,7-dioxa-spiro[5.5]undecan-3-ol

(2R,3R,6S)-3-Methyl-2-[(S)-1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,7-dioxa-spiro[5.5]undecan-3-ol

C₁₃H₂₀O₄

Downstream raw materials:

(R)-2-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-propionaldehyde

(2R,3S,4S)-4-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

(2S,3S,4S)-4-((2R,3R,6S)-3-Benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-3-hydroxy-2-methyl-pentanoic acid methyl ester

(2R,3S,4S)-3-Acetoxy-4-((2R,3R,6S)-3-benzyloxy-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2-methyl-pentanoic acid methyl ester