toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-hydroxy-propyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-hydroxy-propyl ester
• CAS No.: 186355-42-0
• Molecular Formula: C₃₄H₄₁N₃O₉S
• Molecular Weight: 667.78

Synonyms:toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-hydroxy-propyl ester

Chemical Property of toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-hydroxy-propyl ester

Chemical Property:

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Technology Process of toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-hydroxy-propyl ester

There total 11 articles about toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-hydroxy-propyl 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: 88.0%

p-toluenesulfonyl chloride (98-59-9) + [6-benzyloxy-4-tert-butoxycarbonylamino-2-cyano-3-(2,3-dihydroxy-propyl)-phenyl]-carbamic acid tert-butyl ester (186355-41-9) → toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-hydroxy-propyl ester (186355-42-0)

Guidance literature:

[6-benzyloxy-4-tert-butoxycarbonylamino-2-cyano-3-(2,3-dihydroxy-propyl)-phenyl]-carbamic acid tert-butyl ester; With di(n-butyl)tin oxide; In toluene; for 4h; Heating;

p-toluenesulfonyl chloride; With triethylamine; In toluene; at 25 ℃; for 10h;

DOI:10.1021/ja962431g

Reference yield:

2-benzyloxy-4-nitro-phenylamine (25945-96-4) → toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-hydroxy-propyl ester (186355-42-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / NBS

2.1: 95 percent

3.1: 100 percent / Al-Hg

4.1: 82 percent

5.1: 88 percent / TFA

6.1: 92 percent / Pb(OAc)4

7.1: 71 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

8.1: 96 percent / NMMO / OsO₄ / acetone; H₂O / 25 °C

9.1: Bu₂SnO / toluene / 4 h / Heating

9.2: 88 percent / Et₃N / toluene / 10 h / 25 °C

With lead(IV) acetate; N-Bromosuccinimide; aluminium amalgam; boron trifluoride diethyl etherate; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; osmium(VIII) oxide; In dichloromethane; water; acetone; toluene; 1.1: Bromination / 2.1: Substitution / 3.1: Reduction / 4.1: alkoxycarbonylation / 5.1: dealkoxycarbonylation / 6.1: Oxidation / 7.1: Addition / 8.1: hydroxylation / 9.1: Addition / 9.2: Tosylation;

DOI:10.1021/ja962431g

Reference yield:

2-(benzyloxy)-6-bromo-4-nitro-aniline (127028-17-5) → toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-hydroxy-propyl ester (186355-42-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 95 percent

2.1: 100 percent / Al-Hg

3.1: 82 percent

4.1: 88 percent / TFA

5.1: 92 percent / Pb(OAc)4

6.1: 71 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

7.1: 96 percent / NMMO / OsO₄ / acetone; H₂O / 25 °C

8.1: Bu₂SnO / toluene / 4 h / Heating

8.2: 88 percent / Et₃N / toluene / 10 h / 25 °C

With lead(IV) acetate; aluminium amalgam; boron trifluoride diethyl etherate; di(n-butyl)tin oxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; osmium(VIII) oxide; In dichloromethane; water; acetone; toluene; 1.1: Substitution / 2.1: Reduction / 3.1: alkoxycarbonylation / 4.1: dealkoxycarbonylation / 5.1: Oxidation / 6.1: Addition / 7.1: hydroxylation / 8.1: Addition / 8.2: Tosylation;

DOI:10.1021/ja962431g

upstream raw materials:

p-toluenesulfonyl chloride

[6-benzyloxy-4-tert-butoxycarbonylamino-2-cyano-3-(2,3-dihydroxy-propyl)-phenyl]-carbamic acid tert-butyl ester

2-benzyloxy-4-nitro-phenylamine

2-(benzyloxy)-6-bromo-4-nitro-aniline

Downstream raw materials:

toluene-4-sulfonic acid 3-(4-benzyloxy-3,6-bis-tert-butoxycarbonylamino-2-cyano-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-propyl ester

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