Benzyl mercaptan → HCID 68537796, compound

HRID 1993083Notes

Reaction equation

HRID 1993083 reaction equation
C(O[C@@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1OC=CCC)(=O)C.C(S)C1C=CC=CC=1.C([O:40][C@@H:41]1[C@@H:59]([O:60]C(=O)C)[C@H:58]([O:64]C(=O)C)[C@@H:57]([CH2:68][O:69]C(=O)C)[O:56][C@H:42]1[O:43][CH2:44][CH2:45][CH2:46][CH2:47][S:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)(=O)C.C[O-].[Na+]>O1CCOCC1.CC(N=NC(C#N)(C)C)(C#N)C.CO>[O:43]([CH2:44][CH2:45][CH2:46][CH2:47][S:48][CH2:49][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[C@@H:42]1[O:56][C@H:57]([CH2:68][OH:69])[C@@H:58]([OH:64])[C@H:59]([OH:60])[C@H:41]1[OH:40]

Participants

8

Reactant 4

HCID 7509Benzyl mercaptanHCID 10942334Sodium MethoxideHCID 68539732HCID 68539732, compound2×HCID 86596596HCID 86596596, compound

Product 1

HCID 68537796HCID 68537796, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6547AzobisisobutyronitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

4-benzylthiobutyl β-D-glucopyranoside was synthesized by the following reactions from β-D-glucopyranose. Thus, acetyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside was prepared by exhaustive acetylation of the hydroxyl groups in β-D-glucopyranose by the action of sodium acetate in acetic anhydride. The acetyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside was subsequently reacted with 3-buten-1-ol under catalysis by boron trifluoride diethyl etherate to give butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside. The butenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside was mixed with benzyl thiol in dioxane and AIBN was added as radical initiator; reaction then gave 4-benzylthiobutyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside. Deacetylation of the 4-benzylthiobutyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside by reaction with sodium methoxide in methanol gave 4-benzylthiobutyl β-D-glucopyranoside:

Workup

  1. additionwas added as radical initiator
  2. customreaction

Sources & evidence

ORD record
ord-fb48a18b04124edb868353a3e598f671
Source dataset
uspto-grants-2010_01
Patent number
US07649087B2

Reaction notes

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