Toluene-4-sulfonic acid (S)-3-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methoxymethoxy-propyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-3-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methoxymethoxy-propyl ester
• CAS No.: 202339-05-7
• Molecular Formula: C₃₂H₄₀O₁₀S
• Molecular Weight: 616.73
• Mol file: 202339-05-7.mol

Synonyms:Toluene-4-sulfonic acid (S)-3-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methoxymethoxy-propyl ester

Chemical Property of Toluene-4-sulfonic acid (S)-3-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methoxymethoxy-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (S)-3-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methoxymethoxy-propyl ester

There total 11 articles about Toluene-4-sulfonic acid (S)-3-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methoxymethoxy-propyl ester 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: 80.0%

Toluene-4-sulfonic acid (S)-3-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-2-methoxymethoxy-propyl ester (202339-15-9) → Toluene-4-sulfonic acid (S)-3-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methoxymethoxy-propyl ester (202339-05-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1271/bbb.61.2019

Reference yield: 71.0%

Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-[(S)-2-methoxymethoxy-3-(toluene-4-sulfonyloxy)-propyl]-tetrahydro-pyran-3-yl ester (202339-00-2) → Toluene-4-sulfonic acid (S)-3-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methoxymethoxy-propyl ester (202339-05-7)

Guidance literature:

With sodium methylate; In methanol; for 24h; Ambient temperature;

DOI:10.1271/bbb.61.2019

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (S)-3-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-methoxymethoxy-propyl ester (202339-05-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / DMAP / pyridine / 0.5 h / Ambient temperature

2: 79 percent / DIPEA / CH₂Cl₂ / 1 h / 0 °C

3: 71 percent / NaOMe / methanol / 24 h / Ambient temperature

With dmap; sodium methylate; N-ethyl-N,N-diisopropylamine; In pyridine; methanol; dichloromethane;

DOI:10.1271/bbb.61.2019

upstream raw materials:

Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-[(S)-2-methoxymethoxy-3-(toluene-4-sulfonyloxy)-propyl]-tetrahydro-pyran-3-yl ester

Toluene-4-sulfonic acid (S)-3-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-2-methoxymethoxy-propyl ester

p-toluenesulfonyl chloride

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-methoxy-tetrahydro-pyran-3-ol