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-hydroxy-propyl ester

Base Information

• Chemical Name: 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-hydroxy-propyl ester
• CAS No.: 202339-13-7
• Molecular Formula: C₃₈H₄₄O₁₀S
• Molecular Weight: 692.827
• Mol file: 202339-13-7.mol

Synonyms: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-hydroxy-propyl ester

Chemical Property of 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-hydroxy-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-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-2-hydroxy-propyl ester

There total 1 articles about 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-hydroxy-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: 72.0%

p-toluenesulfonyl chloride (98-59-9) + (S)-3-[(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol (202338-80-5) → 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-hydroxy-propyl ester (202339-13-7)

Guidance literature:

With dmap; In pyridine; for 0.5h; Ambient temperature;

DOI:10.1271/bbb.61.2019

Reference yield: 90.0%

chloromethyl methyl ether (107-30-2) + 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-hydroxy-propyl ester (202339-13-7) → 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)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1271/bbb.61.2019

Reference yield:

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-hydroxy-propyl ester (202339-13-7) → (2S,3R,4S,4aR,7S,8aR)-3,4-Bis-benzyloxy-2-methoxy-7-methoxymethoxy-octahydro-pyrano[3,2-b]pyran

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / DIPEA / CH₂Cl₂ / 1 h / 0 °C

2: 80 percent / DDQ / CH₂Cl₂ / 2 h / Ambient temperature

3: 98 percent / 15-crown-5, NaH / dimethylformamide / 0.17 h / Ambient temperature

With 15-crown-5; sodium hydride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb.61.2019

upstream raw materials:

p-toluenesulfonyl chloride

(S)-3-[(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol

Downstream raw materials:

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

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