(1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one

Base Information

Chemical Name:(1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one
CAS No.:389807-34-5
Molecular Formula:C₄₈H₅₃NO₁₀Si
Molecular Weight:832.035
Hs Code.:

Synonyms:(1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one

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Chemical Property of (1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one

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Technology Process of (1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one

There total 13 articles about (1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one 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: 96.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 389807-33-4
(1'S,3S,4S,5S)-3-benzamido-3-hydroxymethyl-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-hydroxyethyl]oxolan-2-one

: 389807-34-5
(1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one

Guidance literature:: With (+)-10-camphorsulfonic acid; In dichloromethane; at 25 ℃; for 18h;
DOI:10.1021/ja0118338

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 389807-34-5
(1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / imidazole

2.1: 67 percent / PCC; Cellite / CH₂Cl₂

3.1: 99 percent / FeCl₃ / CH₂Cl₂ / 0 °C / 0.5 Torr

4.1: NaH / tetrahydrofuran / 25 °C / Irradiation

4.2: (η³-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C

4.3: 68 percent / tetrahydrofuran / 3 h / 0 °C

5.1: 96 percent / (+)-camphorsulfonic acid / diethyl ether / 72 h / 25 °C

6.1: 94 percent / aq. OsO₄; NMO / CH₂Cl₂ / 12 h / 25 °C

7.1: 78 percent / peracetic acid; sodium bromide; sodium acetate / acetic acid / 2.5 h / 25 - 60 °C

8.1: 96 percent / (+)-camphorsulfonic acid / CH₂Cl₂ / 18 h / 25 °C

With 1H-imidazole; peracetic acid; osmium(VIII) oxide; N-methyl-2-indolinone; sodium acetate; silica gel; iron(III) chloride; sodium hydride; (+)-10-camphorsulfonic acid; pyridinium chlorochromate; sodium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; 7.1: modified Fleming oxidation;
DOI:10.1021/ja0118338

Reference yield:

: 101649-82-5
N-benzoyl-2-bromoglycine methyl ester

: 389807-34-5
(1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 61 percent / tetrahydrofuran / 3 h / -78 - 0 °C

2.1: 94 percent / LiOH / tetrahydrofuran; H₂O / 8 h / 25 °C

3.1: 97 percent / DCC / tetrahydrofuran / 12 h / 25 °C

4.1: NaH / tetrahydrofuran / 25 °C / Irradiation

4.2: (η³-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C

4.3: 68 percent / tetrahydrofuran / 3 h / 0 °C

5.1: 96 percent / (+)-camphorsulfonic acid / diethyl ether / 72 h / 25 °C

6.1: 94 percent / aq. OsO₄; NMO / CH₂Cl₂ / 12 h / 25 °C

7.1: 78 percent / peracetic acid; sodium bromide; sodium acetate / acetic acid / 2.5 h / 25 - 60 °C

8.1: 96 percent / (+)-camphorsulfonic acid / CH₂Cl₂ / 18 h / 25 °C

With peracetic acid; lithium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; sodium acetate; sodium hydride; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; sodium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; 7.1: modified Fleming oxidation;
DOI:10.1021/ja0118338