Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester
• CAS No.: 223664-31-1
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445
• Mol file: 223664-31-1.mol

Synonyms:Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester

Chemical Property of Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester

There total 1 articles about Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl 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:

acetic anhydride (108-24-7) + methyl 2,4-di-O-benzyl-3,6-dideoxy-α-D-xylo-hexopyranoside (79726-85-5) → Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester (223664-31-1)

Guidance literature:

With sulfuric acid; acetic acid; at 0 ℃; for 0.833333h;

DOI:10.1021/ol9902374

Reference yield:

(5-tert-butoxymethyl-3-methyl-4,5-dihydro-furan-2-yloxy)-tert-butyl-dimethyl-silane (223664-48-0) + Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester (223664-31-1) → (R)-3-((3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one + (3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one (223664-66-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at 0 ℃;

DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7

Reference yield:

Acetic acid (3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester (223664-31-1) → C38H49O5N3

Guidance literature:

Multi-step reaction with 8 steps

1.1: 10.8 g / TMSOTf; activated molecular sieves 4 Angstroem / CH₂Cl₂; tetrahydrofuran / 1 h / 0 °C

2.1: 5.0 g / TBAF; AcOH / tetrahydrofuran / 2 h / 20 °C

3.1: tetrahydrofuran; diethyl ether / 1 h / -78 - -20 °C

4.1: NaHCO₃; Pb(OAc)4 / CH₂Cl₂ / 0.83 h

5.1: 2-methyl-2-butene; sodium chlorite; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

6.1: 84 percent / Lawesson reagent / toluene / 2.5 h / Heating

7.1: t-BuOK; NIS / benzene; 2-methyl-propan-2-ol / 3.5 h / 20 °C

7.2: 230 mg / triethyl phosphite / xylene / 48 h / Heating

With Lawessons reagent; lead(IV) acetate; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/ol9902374

upstream raw materials:

acetic anhydride

methyl 2,4-di-O-benzyl-3,6-dideoxy-α-D-xylo-hexopyranoside

Downstream raw materials:

(3R,5R)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one

C₂₇H₃₂O₄N₂

C₂₇H₃₆O₆

C₂₆H₃₂O₅