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

Base Information

Chemical Name: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
CAS No.:181270-99-5
Molecular Formula:C₆₁H₆₀O₁₂Si
Molecular Weight:1013.23
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 4 articles about 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 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: 85.0%

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

: 181270-97-3
phenyl 2,3,6-tri-O-benzoyl-4-deoxy-4-C-ethynyl-1-thio-β-D-glucopyranoside

: 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:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In toluene; at 0 ℃; for 0.0833333h;
DOI:10.1002/hlca.19960790505

Reference yield:

: 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

: 181270-99-5
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 4 steps

1: 99 percent / Dess-Martin's periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

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

3: 95 percent / DIBAH / tetrahydrofuran; toluene / 1 h / 0 °C

4: 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; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 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

: 181270-99-5
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