Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-yl ester
CAS No.:181270-92-8
Molecular Formula:C₂₉H₃₀O₇
Molecular Weight:490.553
Hs Code.:

Synonyms:Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-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: 99.0%

: 84218-71-3,114079-12-8,127874-07-1,127875-24-5,127875-31-4,127875-37-0
4-O-acetyl-2,3,6-tri-O-benzyl-β-D-glucopyranoside

: 181270-92-8
Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-yl ester

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1002/hlca.19960790505

Reference yield:

: 181270-92-8
Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-yl ester

: 181270-99-5
O-(2,3,6-tri-O-benzoyl-4-deoxy-4-C-ethynyl-β-D-glucopyranosyl)-(1->6)-3,7-anhydro-4,5,8-tri-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-D-gulo-octitol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) BuLi; 2.) BF₃*OEt₂, Et₃SiH / 1.) THF, -78 deg C, 30 min.; 2.) CH₂Cl₂/MeCN, -20 deg C, 10 min.

2: 95 percent / DIBAH / tetrahydrofuran; toluene / 1 h / 0 °C

3: 85 percent / 4 Angstroem molecular sieves, NIS, TfOH / toluene / 0.08 h / 0 °C

With triethylsilane; N-iodo-succinimide; n-butyllithium; trifluorormethanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; diisobutylaluminium hydride; In tetrahydrofuran; toluene;
DOI:10.1002/hlca.19960790505

Reference yield:

: 181270-92-8
Acetic acid (2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-oxo-tetrahydro-pyran-3-yl ester

: 181270-94-0
(2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-trimethylsilanylethynyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) BuLi; 2.) BF₃*OEt₂, Et₃SiH / 1.) THF, -78 deg C, 30 min.; 2.) CH₂Cl₂/MeCN, -20 deg C, 10 min.

2: 95 percent / DIBAH / tetrahydrofuran; toluene / 1 h / 0 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; diisobutylaluminium hydride; In tetrahydrofuran; toluene;
DOI:10.1002/hlca.19960790505