(4'S)-4'-hydroxy-5'-tosyloxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:(4'S)-4'-hydroxy-5'-tosyloxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
CAS No.:147048-67-7
Molecular Formula:C₂₆H₃₇NO₁₃S
Molecular Weight:603.645
Hs Code.:

Synonyms:(4'S)-4'-hydroxy-5'-tosyloxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

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Chemical Property of (4'S)-4'-hydroxy-5'-tosyloxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

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Technology Process of (4'S)-4'-hydroxy-5'-tosyloxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

There total 7 articles about (4'S)-4'-hydroxy-5'-tosyloxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 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: 69.0%

: 147048-65-5
(4'S)-4',5'-dihydroxypentyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucoside

: 98-59-9
p-toluenesulfonyl chloride

: 147048-67-7
(4'S)-4'-hydroxy-5'-tosyloxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1071/C97175

Reference yield:

: 210765-78-9
(S)-4,5-Bis-benzyloxy-pentanoic acid ethyl ester

: 147048-67-7
(4'S)-4'-hydroxy-5'-tosyloxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / LiAlH₄ / tetrahydrofuran / 0 °C

2: 85 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / Heating

3: 86 percent / hydrogen / 10percent Pd/C / acetic acid; methanol

4: 69 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane;
DOI:10.1071/C97175

Reference yield:

: (Z)-(S)-4,5-Bis-benzyloxy-pent-2-enoic acid ethyl ester

: 147048-67-7
(4'S)-4'-hydroxy-5'-tosyloxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / hydrogen, NH₃ / 10percent Pd/C / methanol

2: 94 percent / LiAlH₄ / tetrahydrofuran / 0 °C

3: 85 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / Heating

4: 86 percent / hydrogen / 10percent Pd/C / acetic acid; methanol

5: 69 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; ammonia; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane;
DOI:10.1071/C97175