(3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ⁶-thia-3-aza-indene-3-carboxylic acid allyl ester

Base Information

• Chemical Name: (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ⁶-thia-3-aza-indene-3-carboxylic acid allyl ester
• CAS No.: 709032-70-2
• Molecular Formula: C₃₁H₃₃NO₉S
• Molecular Weight: 595.67

Synonyms:(3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ⁶-thia-3-aza-indene-3-carboxylic acid allyl ester

Chemical Property of (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ⁶-thia-3-aza-indene-3-carboxylic acid allyl ester

Chemical Property:

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Technology Process of (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ⁶-thia-3-aza-indene-3-carboxylic acid allyl ester

There total 1 articles about (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ⁶-thia-3-aza-indene-3-carboxylic acid allyl 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:

3,4,6-tri-O-benzyl-D-glucopyranose (20672-66-6,40246-26-2,84926-76-1,114179-79-2,115184-49-1) + C10H20N2O4S (439585-15-6) → (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ6-thia-3-aza-indene-3-carboxylic acid allyl ester (709032-70-2) + (3aR,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ6-thia-3-aza-indene-3-carboxylic acid allyl ester

Guidance literature:

In tetrahydrofuran; dichloromethane; for 6h; Heating;

DOI:10.1021/ja049293c

Reference yield: 87.0%

(3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ6-thia-3-aza-indene-3-carboxylic acid allyl ester (709032-70-2) → (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-1,4-dioxa-2-thia-3-aza-indene 2,2-dioxide (709032-87-1)

Guidance literature:

With palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; diethylamine; In water; acetonitrile; at 25 ℃; for 0.5h;

DOI:10.1021/ja049293c

Reference yield:

(3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dioxo-tetrahydro-1,4-dioxa-2λ6-thia-3-aza-indene-3-carboxylic acid allyl ester (709032-70-2) → (3aS,5R,6R,7S,7aR)-3-Allyl-6,7-bis-benzyloxy-5-benzyloxymethyl-hexahydro-1,4-dioxa-2-thia-3-aza-indene 2,2-dioxide

Guidance literature:

Multi-step reaction with 2 steps

1.1: 87 percent / Et₂NH; Pd(OAc)2; TPPTS / acetonitrile; H₂O / 0.5 h / 25 °C

2.1: NaH / dimethylsulfoxide / 0.17 h / 25 °C

2.2: 0.067 g / dimethylsulfoxide / 0.25 h / 25 °C

With palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; sodium hydride; diethylamine; In water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/ja049293c

upstream raw materials:

3,4,6-tri-O-benzyl-D-glucopyranose

C₁₀H₂₀N₂O₄S

Downstream raw materials:

(3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-1,4-dioxa-2-thia-3-aza-indene 2,2-dioxide

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